US20200115406A1 - Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound - Google Patents

Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound Download PDF

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US20200115406A1
US20200115406A1 US16/553,833 US201916553833A US2020115406A1 US 20200115406 A1 US20200115406 A1 US 20200115406A1 US 201916553833 A US201916553833 A US 201916553833A US 2020115406 A1 US2020115406 A1 US 2020115406A1
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alkyl
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bicyclo
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Jeoungin YI
Juhyun Kim
Sangho Park
Sunyoung Lee
Seokhwan HONG
Kyuyoung HWANG
Yoonhyun Kwak
Sunghun Lee
Byoungki CHOI
Hyeonho CHOI
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Samsung Electronics Co Ltd
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Assigned to SAMSUNG ELECTRONICS CO., LTD. reassignment SAMSUNG ELECTRONICS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHOI, BYOUNGKI, CHOI, HYEONHO, HONG, SEOKHWAN, HWANG, KYUYOUNG, KIM, JUHYUN, KWAK, YOONHYUN, LEE, SUNGHUN, LEE, SUNYOUNG, PARK, SANGHO, YI, JEOUNGIN
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Definitions

  • An embodiment relates to an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the organometallic compound.
  • OLEDs are self-emission devices, which have superior characteristics in terms of a viewing angle, a response time, a brightness, a driving voltage, and a response speed, and which produce full-color images.
  • an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer.
  • a hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode.
  • Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region.
  • the holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
  • luminescent compounds may be used to monitor, sense, or detect a variety of biological materials including cells and proteins.
  • An example of the luminescent compounds includes a phosphorescent luminescent compound.
  • aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the organometallic compound.
  • An aspect of the present disclosure provides an organometallic compound represented by Formula 1:
  • an organic light-emitting device including:
  • the organometallic compound included in the emission layer in the organic layer may act as a dopant.
  • Another aspect of the present disclosure provides a diagnostic composition including an organometallic compound represented by Formula 1.
  • FIGURE is a schematic view of an organic light-emitting device according to an embodiment.
  • first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.
  • Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
  • “About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ⁇ 30%, 20%, 10%, 5% of the stated value.
  • an organometallic compound is provided.
  • the organometallic compound according to an embodiment may be represented by Formula 1:
  • M may be a transition metal.
  • M may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).
  • M may be Pt, Pd, or Au.
  • X 1 may be O or S, wherein a bond between X 1 and M may be a covalent bond.
  • X 1 may be O.
  • X 2 to X 4 may each independently be C or N.
  • X 2 and X 3 may each independently be C or N, and X 4 may be N.
  • X 2 and X 4 may each be N, and X 3 may be C, but embodiments of the present disclosure are not limited thereto.
  • a bond between X 2 and M, a bond between X 3 and M, or a bond between X 4 and M may be a covalent bond, and the other bonds of a bond between X 2 and M, a bond between X 3 and M, and a bond between X 4 and M may be coordinate bonds. Therefore, the organometallic compound represented by Formula 1 may be electrically neutral.
  • a bond between X 2 and M and a bond between X 4 and M may be a coordinate bond, and a bond between X 3 and M may be a covalent bond, but embodiments of the present disclosure are not limited thereto.
  • Y 1 and Y 3 to Y 5 may each independently be C or N.
  • Y 1 and Y 3 to Y 5 may be C.
  • a bond between X 2 and Y 3 , a bond between X 2 and Y 4 , and a bond between Y 4 and Y 5 may be a chemical bond (for example, a single bond, a double bond, or the like).
  • ring CY 1 to ring CY 4 and ring CY 51 may each independently be a C 5 -C 30 carbocyclic group or a C 2 -C 30 heterocyclic group.
  • ring CY 1 to ring CY 4 and ring CY 51 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which a first ring and a second ring are condensed.
  • the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a di
  • ring CY 1 to ring CY 4 and ring CY 51 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group,
  • ring CY 4 may not be a benzimidazole group.
  • a cyclometalated ring formed by ring CY 5 , ring CY 2 , ring CY 3 , and M may be a 6-membered ring.
  • T 1 may be a single bond, but embodiments of the present disclosure are not limited thereto.
  • L 1 to L 4 and L 51 may each independently be a single bond, a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group, or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group.
  • R 10a is defined the same as R 1 .
  • L 1 to L 4 and L 51 may each independently be:
  • L 1 to L 4 and L 51 may each independently be:
  • Y 1 and X 3 may be C, and X 2 and X 4 may be N,
  • ring CY 1 to ring CY 3 and ring CY 51 may be a benzene group
  • ring CY 4 may be a pyridine group
  • L 4 and L 51 may each independently be:
  • b1 to b4 and b51 each indicate the number of L 1 to L 4 and L 51 , respectively, and may each independently be an integer from 1 to 5.
  • two or more L 1 groups may be identical to or different from each other
  • two or more L 2 groups may be identical to or different from each other
  • b3 is two or more
  • two or more L 3 groups may be identical to or different from each other
  • b4 is two or more
  • two or more L 4 groups may be identical to or different from each other
  • b51 is two or more, two or more L 51 groups may be identical to or different from each other.
  • b1 to b4 and b51 may each independently be 1, 2 or 3, but embodiments of the present disclosure are not limited thereto.
  • R 1 to R 6 , R 51 , and R 52 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted
  • R 1 to R 6 , R 51 , and R 52 may each independently be:
  • c1 to c4, c51, and c52 each indicate the number of R 1 to R 4 , R 51 , and R 52 , respectively, and may each independently be an integer from 1 to 5.
  • c1 is two or more, two or more R 1 groups may be identical to or different from each other
  • c2 is two or more
  • two or more R 2 groups may be identical to or different from each other
  • c3 is two or more
  • two or more R 3 groups may be identical to or different from each other
  • c4 is two or more
  • two or more R 4 groups may be identical to or different from each other
  • c51 is two or more
  • two or more R 51 groups may be identical to or different from each other
  • c52 is two or more, two or more R 52 groups may be identical to or different from each other.
  • c1 to c4, c51, and c52 may each independently be 1 or 2, but embodiments of the present disclosure are not limited thereto.
  • a 51 may be a C 4 -C 60 alkyl group
  • a 52 may be deuterium or a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group.
  • a 51 may be a linear or branched C 4 -C 10 alkyl group
  • a 52 may be deuterium or a deuterium-containing linear or branched C 1 -C 20 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group.
  • a 51 may be an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-iso-pentyl group, unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-butyl group,
  • a 52 may be a deuterium-containing linear or branched C 1 -C 20 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group, in which the linear or branched C 1 -C 20 alkyl group may be a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-iso-pentyl group, unsubstituted or substituted with a methyl group, an ethyl group, an n-
  • the deuterium-containing C 1 -C 60 alkyl group (or, the deuterium-containing C 1 -C 20 alkyl group, the deuterium-containing C 2 -C 20 alkyl group, etc.) means a C 1 -C 60 alkyl group substituted with a deuterium (or, a C 1 -C 20 alkyl group substituted with a deuterium, a C 2 -C 20 alkyl group substituted with a deuterium, etc.).
  • a deuterium-containing C 1 alkyl group (that is, a deuterium-containing methyl group) includes —CD 3 , —CD 2 H and —CDH 2 .
  • the deuterium-containing C 1 -C 60 alkyl group (or, the deuterium-containing C 1 -C 20 alkyl group, the deuterium-containing C 2 -C 20 alkyl group, etc.) may be additionally substituted with a C 3 -C 10 cycloalkyl group.
  • Formula 9-619 is a group corresponding to —CD 2 H, in which “—H” is substituted with a cyclopentyl group.
  • the organometallic compound represented by Formula 1 may include a deuterium, a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group, or any combination thereof.
  • the number of deuterium atoms in the organometallic compound represented by Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • Formula 1 may be a group represented by one of Formulae 10-10 to 10-118, or a group represented by one of Formulae 10-10 to 10-118 in which a hydrogen is substituted with deuterium:
  • the “group represented by one of Formulae 9-1 to 9-66 in which a hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 or 9-601 to 9-638.
  • the “group represented by one of Formulae 10-1 to 10-118 in which a hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-552:
  • a 52 may be a group represented by one of Formulae 9-1 to 9-36 in which all hydrogens are substituted with deuterium, but embodiments of the present disclosure are not limited thereto.
  • a1 to a4, a51, and a52 each indicate the number of *-[(L 1 ) b1 -(R 1 ) c1 ], *-[(L 2 ) b2 -(R 2 ) c2 ], *-[(L 3 ) b3 -(R 3 ) c3 ], *-[(L 4 ) b4 -(R 4 ) c4 ], A 51 , and A 52 , respectively, and may each independently be an integer from 0 to 10.
  • two or more *-[(L 1 ) b1 -(R 1 ) c1 ] groups may be identical to or different from each other
  • two or more *-[(L 2 ) b2 -(R 2 ) c2 ] groups may be identical to or different from each other
  • a3 is two or more
  • two or more *-[(L 3 ) b3 -(R 3 ) c3 ] groups may be identical to or different from each other
  • a4 is two or more
  • two or more *-[(L 4 ) b4 -(R 4 ) c4 ] groups may be identical to or different from each other
  • a51 is two or more
  • two or more A 51 groups may be identical to or different from each other
  • two or more A 52 groups may be identical to or different from each other, but embodiments of the present disclosure are not limited thereto.
  • a1 to a4, a51, and a52 may each independently be 0, 1, 2, 3, 4, 5, or 6, but embodiments of the present disclosure are not limited thereto.
  • a1 and a4 may each independently be 0, 1, 2, 3, or 4 and a2, a3, a51 and a52 may each independently be 0, 1, 2, or 3.
  • a51 and a52 may be 1 or more. That is, in Formula 1, ring CY 51 may be substituted with a group represented by A 51 , a group represented by A 52 , or any combination thereof.
  • the sum of a51 and a52 may be 1, 2, or 3. In an embodiment, the sum of a51 and a52 may be 1 or 2.
  • Formula 1 is substituted with a group represented by
  • a3, and a4 may not be 0, and a group represented by *-(L 3 ) b3 -(R 3 ) c3 , and a group represented by *-(L 4 ) b4 -(R 4 ) c4 may not be hydrogen.
  • a1, a3, and a4 may not be 0, and a group represented by *-(L 1 ) b1 -(R 1 ) c1 , a group represented by *-(L 3 ) b3 -(R 3 ) c3 , and a group represented by *-(L 4 ) b4 -(R 4 ) c4 may not be hydrogen.
  • a1 may not be 0, a group represented by *-(L 1 ) b1 -(R 1 ) c1 may not be hydrogen, and a group represented by *-(L 1 ) b1 -(R 1 ) c1 in a number of a1 may include a deuterium.
  • a1 may be 2
  • two groups represented by *-(L 1 ) b1 -(R 1 ) c1 may not be hydrogen
  • two groups represented by *-(L 1 ) b1 -(R 1 ) c1 may be identical to each other.
  • a1 may be 2, two groups represented by *-(L 1 ) b1 -(R 1 ) c1 may not be hydrogen, and two groups represented by *-(L 1 ) b1 -(R 1 ) c1 may be different from each other.
  • a4 may not be 0, a group represented by *-(L 4 ) b4 -(R 4 ) c4 may not be hydrogen, and a group represented by *-(L 4 ) b4 -(R 4 ) c4 in a number of a4 may include a deuterium.
  • a3 may not be 0, and a group represented by *-(L 3 ) b3 -(R 3 ) c3 in a number of a3 may satisfy Condition A and Condition B:
  • R 3 may not hydrogen
  • a3 may not be 0, and a group represented by *-(L 3 ) b3 -(R 3 ) c3 in a number of a3 may satisfy Condition A and Condition B(1):
  • a4 may not be 0, and a group represented by *-(L 4 ) b4 -(R 4 ) c4 in a number of a4 may satisfy Condition 1, Condition 2, or combination thereof:
  • a4 may not be 0, and a group represented by *-(L 4 ) b4 -(R 4 ) c4 in a number of a4 may satisfy Condition 1(1), Condition 2(1), or combination thereof:
  • a4 may not be 0, and a group represented by *-(L 4 ) b4 -(R 4 ) c4 in a number of a4 may satisfy Condition 3, Condition 4, Condition 5, or combination thereof:
  • a4 may not be 0, and a group represented by *-(L 4 ) b4 -(R 4 ) c4 in a number of a4 may satisfy Condition 3(1), Condition 4(1), Condition 5(1), or combination thereof:
  • a51 and a52 may each independently be 0, 1 or 2
  • the sum of a51 and a52 may be 1 or 2
  • a53 may be 1 or 2.
  • * and *′ each indicate a binding site to a neighboring atom.
  • Formula 1 may be a group represented by one of Formulae A1(1) to A1(30):
  • Formula 1 may include deuterium, a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group, or any combination thereof.
  • Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • Formula 1 may be a group represented by one of Formulae A2(1) to A2(4):
  • Formula 1 may include deuterium, a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group, or any combination thereof.
  • Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • Formula 1 may be a group represented by one of Formulae A3(1) to A3(17):
  • Formula 1 may include deuterium, a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group, or any combination thereof.
  • Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • Formula 1 may be a group represented by one of Formulae A4(1) to A4(45):
  • Formula 1 may include deuterium, a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group, or any combination thereof.
  • Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • CY1(1) to CY1(8) may be a group represented by one of Formulae CY1(1) to CY1(8), and/or
  • CY2(1) to CY2(4) may be a group represented by one of Formulae CY2(1) to CY2(4), and/or
  • CY3(1) to CY3(24) may be a group represented by one of Formulae CY3(1) to CY3(24), and/or
  • CY4-1 may be a group represented by Formula CY4-1 or CY4-2:
  • Formulae CY4-1 and CY4-2 may satisfy:
  • Condition 1 Condition 1, Condition 2, or any combination thereof (or, Condition 1(1), Condition 2(1), or any combination thereof), and/or
  • Condition 3 Condition 4, Condition 5, or any combination thereof (or, Condition 3(1), Condition 4(1), Condition 5(1), or any combination thereof).
  • CY1(1) or CY1(6) may be a group represented by Formula CY1(1) or CY1(6), and/or
  • CY4(3) may be a group represented by Formula CY4(3), CY4(4) or CY4(16).
  • Formula 1 may be a group represented by one of Formulae 51-1 to 51-32:
  • R 51 , R 52 , c52, A 51 , and A 52 may each independently be the same as described herein, R 53 and c53 may each independently be the same as described in connection with R 52 and c52, c512 is an integer of 0 to 2, c513 is an integer of 0 to 3, and * indicates a binding site to L 51 .
  • the organometallic compound may be represented by Formula 1-1 or 1-2:
  • M, X 1 to X 4 , Y 1 , Y 3 to Y 5 , L 4 , L 51 , b4, b51, R 51 , R 52 , c51, c52, A 51 , A 52 , a51, a52 and a53 may each independently be the same as described herein,
  • Z 11 to Z 14 may each independently be the same as described in connection with R 1 ,
  • Z 21 to Z 23 may each independently be the same as described in connection with R 2 ,
  • Z 31 to Z 33 may each independently be the same as described in connection with R 3 ,
  • Z 41 to Z 44 may each independently be the same as described in connection with R 4 ,
  • two or more groups of Z 11 to Z 14 may be optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group,
  • two or more groups of Z 21 to Z 23 may be optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group,
  • two or more groups of Z 31 to Z 33 may be optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group,
  • two or more groups of Z 41 to Z 44 may be optionally linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group, and
  • Formulae 1-1 and 1-2 may satisfy Condition A, Condition B, or any combination thereof (or, Condition A, Condition B(1), or any combination thereof), and/or
  • Formulae 1-1 and 1-2 may satisfy Condition 1, Condition 2, or any combination thereof (or, Condition 1(1), Condition 2(1), or any combination thereof), and/or
  • Formulae 1-1 and 1-2 may satisfy Condition 3, Condition 4, Condition 5, or any combination thereof (or, Condition 3(1), Condition 4(1), Condition 5(1), or any combination thereof), and/or
  • Formulae 1-1 and 1-2 may be a group represented by one of Formulae 51-1 to 51-32.
  • Z 12 , Z 14 , Z 21 to Z 23 , Z 31 , Z 33 and Z 41 to Z 44 in Formulae 1-1 and 1-2 may each independently be hydrogen, deuterium, —CH 3 , or —CD 3 .
  • Z 12 , Z 14 , Z 21 to Z 23 , Z 31 , Z 33 and Z 41 to Z 44 in Formulae 1-1 and 1-2 may each independently be hydrogen, or deuterium.
  • Z 11 and Z 13 in Formulae 1-1 and 1-2 may not be hydrogen and Z 11 and Z 13 may include a deuterium.
  • Z 11 and Z 13 in Formulae 1-1 and 1-2 may not be hydrogen and Z 11 and Z 13 may be identical to each other.
  • Z 11 and Z 13 in Formulae 1-1 and 1-2 may not be hydrogen and Z 11 and Z 13 may be different from each other.
  • two or more groups of a plurality of R 1 groups may optionally be linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group
  • two or more groups of a plurality of R 2 groups may optionally be linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group
  • two or more groups of a plurality of R 3 groups may optionally be linked to form a C 5 -C 30 carbocyclic group that is unsubstituted or substituted with an R 10a group or a C 2 -C 30 heterocyclic group that is unsubstituted or substituted with an R 10a group
  • a C 5 -C 30 carbocyclic group (that is unsubstituted or substituted with an R 10a group) and a C 2 -C 30 heterocyclic group (that is unsubstituted or substituted with an R 10a group) may each independently be a cyclopentane group, a silole group, an azasilole group, a diazasilole group, a triazasilole group, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a
  • Non-limiting examples of the C 1 -C 60 alkyl group, C 1 -C 20 alkyl group and/or C 1 -C 10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a ter
  • Non-limiting examples of the C 1 -C 60 alkoxy group, C 1 -C 20 alkoxy group and/or C 1 -C 10 alkoxy group include a methoxy group, an ethoxy group, a propoxy group or a butoxy group, and the like, but embodiments of the present disclosure are not limited thereto.
  • Non-limiting examples of the C 3 -C 10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, and the like, but embodiments of the present disclosure are not limited thereto.
  • An angle formed by a plane including the transition dipole moment of the organometallic compound represented by Formula 1 and a plane including four atoms of a tetradentate ligand linked to a metal M of Formula 1 may be about 10° or less.
  • a horizontal orientation ratio of the transition dipole moment of the organometallic compound represented by Formula 1 may be in a range of about 80% to about 100%.
  • the angle formed by the plane including the transition dipole moment of the organometallic compound and the plane including the four atoms of the tetradentate ligand linked to the metal (or platinum) of Formula 1 may be 0° to 10°, 0° to 9°, 0° to 8°, 0° to 7°, 0° to 6°, 0° to 5°, 0° to 4°, 0° to 3°, 0° to 2°, or 0° to 1°, but embodiments of the present disclosure are not limited thereto.
  • the organometallic compound When the angle formed by the plane including the transition dipole moment of the organometallic compound represented by the Formula 1 and the plane including the four atoms of the tetradentate ligand linked to the metal of Formula 1 is within these ranges, the organometallic compound may have excellent planarity, and a thin film formed by using the organometallic compound may have excellent electric characteristics.
  • the horizontal orientation ratio of the transition dipole moment of the organometallic compound may be in a range of, for example, 80% to 100%, 81% to 100%, 82% to 100%, 83% to 100%, 84% to 100%, 85% to 100%, 86% to 100%, 87% to 100%, 88% to 100%, 89% to 100%, 90% to 100%, 91% to 100%, 92% to 100%, 93% to 100%, 94% to 100%, 95% to 100%, 96% to 100%, 97% to 100%, 98% to 100%, 99% to 100%, or 100%, but embodiments of the present disclosure are not limited thereto.
  • the horizontal orientation ratio of the transition dipole moment means a ratio of the organometallic compound having a transition dipole moment horizontal to the film including the organometallic compound to the total organometallic compound in the film including the organometallic compound.
  • the horizontal orientation ratio of the transition dipole moment may be evaluated by using an angle-dependent PL measurement apparatus.
  • the angle-dependent PL measurement apparatus may be understood by referring to Korean Patent Application No. 10-2013-0150834, the content of which is incorporated herein in its entirety by reference.
  • the organometallic compound Since the organometallic compound has a high horizontal orientation ratio of a transition dipole moment, the organometallic compound has a large horizontal orientation transition dipole moment (that is, a large horizontal optical orientation). Therefore, a large amount of electric field traveling in a direction perpendicular to the film including the organometallic compound may be emitted.
  • Light emitted due to such a mechanism may have high external extraction efficiency (that is, efficiency of extracting light emitted in the organometallic compound from a device (for example, an organic light-emitting device) including a film (for example, an emission layer described below) including the organometallic compound) to the outside, and thus, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound, may have high luminescent efficiency.
  • a device for example, an organic light-emitting device
  • a film for example, an emission layer described below
  • R 10a is defined the same as R 1 .
  • the organometallic compound represented by Formula 1 may include a deuterium.
  • the organometallic compound may be one of the following Compounds 1 to 3599:
  • a 51 may be a C 4 -C 60 alkyl group
  • a 52 may be deuterium or a deuterium-containing C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group
  • a51 (the number of A 51 ) and a52 (the number of A 52 ) may each independently be an integer from 0 to 10, provided that the sum of a51 and a52 may be 1 or more. That is, in Formula 1, ring CY 51 is substituted with a group represented by A 51 , a group represented by A 52 , or any combination thereof. Since ring CY 51 is substituted with an electron donating group, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan.
  • a 51 in Formula 1 may be a group having the formula —C(R 511 )(R 512 )(R 513 ), wherein R 511 , R 512 , and R 513 are each independently a C 1 -C 60 alkyl group, for example, a C 1 -C 50 alkyl group, a C 1 -C 40 alkyl group, a C 1 -C 30 alkyl group, a C 1 -C 20 alkyl group, a C 1 -C 10 alkyl group, or a C 1 -C 5 alkyl group.
  • the organometallic compound represented by Formula 1 may have improved luminescent efficiency and lifespan compared to the compounds in which at least one of R 511 , R 512 , or R 513 is hydrogen.
  • a 52 in Formula 1 may be a group having the formula —CD(R 521 )(R 522 ), wherein R 521 and R 522 are each independently a C 1 -C 60 alkyl group, a C 1 -C 60 alkyl group substituted with deuterium, a C 3 -C 10 cycloalkyl group, or any combination thereof.
  • a 52 in Formula 1 may be a group having the formula —CD 2 (R 521 ), wherein R 521 is the same as defined above.
  • a 52 may be a fully deuterated group, such as CD 3 , C 2 D 5 , C 3 D 7 , C 4 D 9 , but is not limited thereto.
  • the organometallic compound represented by Formula 1 may have improved luminescent efficiency and lifespan compared to the compounds in which at least one of R 521 or R 522 is hydrogen.
  • a 52 may be a partially or fully deuterated C 1 -C 60 alkyl group unsubstituted or substituted with a C 3 -C 10 cycloalkyl group. When the degree of deuteration is 100%, the group A 52 is fully deuterated. When the degree of deuteration is lower than 100%, the group A 52 is partially deuterated. The degree of deuteration of the group A 52 may be calculated by using Equation 10:
  • n H2 represents the total number of hydrogens included in the group A 52 .
  • n D2 represents the total number of deuterium atoms included in the group A 52 .
  • the degree of deuteration of the group A 52 may be about 5% or more, about 10% or more, about 20% or more, about 30% or more, about 40% or more, about 50% or more, about 60% or more, about 70% or more, about 90% or more, about 95% or more, about 96% or more, about 97% or more, about 98% or more, or about 99% or more, but embodiments of the present disclosure are not limited thereto.
  • Formula 1 may be an integer from 1 to 10. That is, since a53 in Formula 1 is not 0, ring CY 51 in Formula 1 is substituted with a group represented by
  • an electronic device for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan.
  • an organic light-emitting device which includes the organometallic compound represented by Formula 1
  • an electronic device for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan.
  • the organometallic compound may simultaneously include
  • the organometallic compound may simultaneously include
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • Si singlet
  • Ti triplet
  • the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.
  • Synthesis methods of the organometallic compound represented by Formula 1 may be understood by one of ordinary skill in the art by referring to Synthesis Examples provided below.
  • the organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer.
  • an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer and an organometallic compound represented by Formula 1.
  • the organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1, a low driving voltage, high quantum efficiency, a low roll-off ratio, and a long lifespan.
  • the organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device.
  • the organometallic compound represented by Formula 1 may be included in the emission layer.
  • the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).
  • the emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
  • the organometallic compound represented by Formula 1 may be a red phosphorescent dopant.
  • (an organic layer) includes an organometallic compound as used herein may include an embodiment in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and an embodiment in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1.”
  • the organic layer may include, as the organometallic compound, only Compound 1.
  • Compound 1 may be included in an emission layer of the organic light-emitting device.
  • the organic layer may include, as the organometallic compound, Compound 1 and Compound 2.
  • Compound 1 and Compound 2 may be included in an identical layer (for example, Compound 1 and Compound 2 may both be included in an emission layer).
  • the first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the organic layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • organic layer refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device.
  • the “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
  • the FIGURE is a schematic view of an organic light-emitting device 10 according to an embodiment.
  • the organic light-emitting device 10 includes a first electrode 11 , an organic layer 15 , and a second electrode 19 , which are sequentially stacked.
  • a substrate may be additionally disposed under the first electrode 11 or above the second electrode 19 .
  • the substrate any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • the first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate.
  • the first electrode 11 may be an anode.
  • the material for forming the first electrode 11 may be a material(s) with a high work function to facilitate hole injection.
  • the first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode.
  • the material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), and zinc oxide (ZnO).
  • magnesium (Mg), aluminum (Al), aluminum-lithium (Al-L 1 ), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the first electrode.
  • the first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers.
  • the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
  • the organic layer 15 is disposed on the first electrode 11 .
  • the organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
  • the hole transport region may be disposed between the first electrode 11 and the emission layer.
  • the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
  • the hole transport region may include only either a hole injection layer or a hole transport layer.
  • the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11 .
  • a hole injection layer may be formed on the first electrode 11 by using a suitable method for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or any combination thereof.
  • LB Langmuir-Blodgett
  • the deposition conditions may vary according to a compound that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer.
  • the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10 ⁇ 8 torr to about 10 ⁇ 3 torr, and a deposition rate of about 0.01 Angstroms per second ( ⁇ /sec) to about 100 ⁇ /sec.
  • the deposition conditions are not limited thereto.
  • coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer.
  • a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm
  • a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C.
  • the coating conditions are not limited thereto.
  • Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
  • the hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, ⁇ -NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4′′-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
  • Ar 101 and Ar 102 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group
  • xa and xb may each independently be an integer from 0 to 5, or may be 0, 1, or 2.
  • xa is 1 and xb is 0, but xa and xb are not limited thereto.
  • R 101 to R 108 , R 111 to R 119 , and R 121 to R 124 may each independently be:
  • a C 1 -C 10 alkyl group or a C 1 -C 10 alkoxy group each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or any combination thereof; or
  • a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group or any combination thereof,
  • R 109 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.
  • the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:
  • R 101 , R 111 , R 112 , and R 109 are each independently the same as described above.
  • the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include Compounds HT1 to HT20, but are not limited thereto:
  • a thickness of the hole transport region may be in a range of about 100 Angstroms ( ⁇ ) to about 10,000 ⁇ , for example, about 100 ⁇ to about 1,000 ⁇ .
  • the thickness of the hole injection layer may be in a range of about 100 ⁇ to about 10,000 ⁇ , and for example, about 100 ⁇ to about 1,000 ⁇
  • the thickness of the hole transport layer may be in a range of about 50 ⁇ to about 2,000 ⁇ , and for example, about 100 ⁇ to about 1,500 ⁇ . While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
  • the hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties.
  • the charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
  • the charge-generation material may be, for example, a p-dopant.
  • the p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto.
  • Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D 1 , but are not limited thereto.
  • a quinone derivative such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ)
  • a metal oxide such as a tungsten oxide or a molybdenum oxide
  • a cyano group-containing compound such as Compound HT-D 1 , but are not limited thereto.
  • the hole transport region may include a buffer layer.
  • the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
  • a material for the electron blocking layer may be a material(s) for the hole transport region described above and materials for a host to be explained later.
  • the material for the electron blocking layer is not limited thereto.
  • a material for the electron blocking layer may be mCP, which will be explained later.
  • an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like.
  • the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.
  • the emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
  • the host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or any combination thereof:
  • the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer.
  • the emission layer may emit white light.
  • an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
  • the dopant may include the organometallic compound represented by Formula 1.
  • the dopant may be a red phosphorescent dopant.
  • a thickness of the emission layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , for example, about 200 ⁇ to about 600 ⁇ . While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
  • an electron transport region may be disposed on the emission layer.
  • the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto.
  • the electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
  • Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
  • the hole blocking layer may include, for example, BCP, Bphen, BAIq, or any combination thereof, but embodiments of the present disclosure are not limited thereto:
  • a thickness of the hole blocking layer may be in a range of about 20 ⁇ to about 1,000 ⁇ , for example, about 30 ⁇ to about 300 ⁇ . While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking ability without a substantial increase in driving voltage.
  • the electron transport layer may include BCP, Bphen, Alq 3 , BAIq, TAZ, NTAZ, or any combination thereof:
  • the electron transport layer may include at least one of ET1 to ET25, but are not limited thereto:
  • a thickness of the electron transport layer may be in a range of about 100 ⁇ to about 1,000 ⁇ , for example, about 150 ⁇ to about 500 ⁇ . While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
  • the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
  • the metal-containing material may include a L 1 complex.
  • the L 1 complex may include, for example, Compound ET-D 1 (lithium 8-hydroxyquinolate, LiQ) or ET-D 2 :
  • the electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.
  • the electron injection layer may include LiF, NaCl, CsF, L 12 O, BaO, or any combination thereof.
  • a thickness of the electron injection layer may be in a range of about 1 ⁇ to about 100 ⁇ , for example, about 3 ⁇ to about 90 ⁇ . While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
  • the second electrode 19 is disposed on the organic layer 15 .
  • the second electrode 19 may be a cathode.
  • a material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or any combination thereof, which have a relatively low work function.
  • lithium (L 1 ), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-L 1 ), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as a material for forming the second electrode 19 .
  • a transmissive electrode formed using ITO or IZO may be used as the second electrode 19 .
  • Another aspect of the present disclosure provides a diagnostic composition including an organometallic compound represented by Formula 1.
  • the organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
  • the diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
  • C 1 -C 60 alkyl group refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.
  • C 1 -C 60 alkylene group refers to a divalent group having the same structure as the C 1 -C 60 alkyl group.
  • C 1 -C 60 alkoxy group refers to a monovalent group represented by —OA 101 (wherein A 101 is the C 1 -C 60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy group.
  • C 2 -C 60 alkenyl group refers to a hydrocarbon group formed by including a carbon-carbon double bond in the middle or at the terminus of the C 2 -C 60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group.
  • C 2 -C 60 alkenylene group refers to a divalent group having the same structure as the C 2 -C 60 alkenyl group.
  • C 2 -C 60 alkynyl group refers to a hydrocarbon group formed by including a carbon-carbon triple bond in the middle or at the terminus of the C 2 -C 60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group.
  • C 2 -C 60 alkynylene group refers to a divalent group having the same structure as the C 2 -C 60 alkynyl group.
  • C 3 -C 10 cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • C 3 -C 10 cycloalkylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkyl group.
  • C 2 -C 10 heterocycloalkyl group refers to a monovalent saturated monocyclic group having an N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group.
  • C 2 -C 10 heterocycloalkylene group refers to a divalent group having the same structure as the C 2 -C 10 heterocycloalkyl group.
  • C 3 -C 10 cycloalkenyl group refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and a carbon-carbon double bond in the ring thereof and that has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group.
  • C 3 -C 10 cycloalkenylene group refers to a divalent group having the same structure as the C 3 -C 10 cycloalkenyl group.
  • C 2 -C 10 heterocycloalkenyl group refers to a monovalent monocyclic group that has an N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom, 1 to 10 carbon atoms, and a carbon-carbon double bond in its ring.
  • Examples of the C 2 -C 10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group.
  • C 1 -C 10 heterocycloalkenylene group refers to a divalent group having the same structure as the C 2 -C 10 heterocycloalkenyl group.
  • C 6 -C 60 aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms
  • C 6 -C 60 arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms.
  • Non-limiting examples of the C 6 -C 60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group.
  • the C 6 -C 60 aryl group and the C 6 -C 60 arylene group each include two or more rings, the rings may be fused to each other.
  • C 7 -C 60 alkylaryl group refers to a C 1 -C 60 aryl group substituted with a C 1 -C 54 alkyl group.
  • C 1 -C 60 heteroaryl group refers to a monovalent group having an aromatic system that has an N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms.
  • C 1 -C 60 heteroarylene group refers to a divalent group having an aromatic system that has an N, O, P, Se, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms.
  • Non-limiting examples of the C 1 -C 60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.
  • the C 1 -C 60 heteroaryl group and the C 1 -C 60 heteroarylene group each include two or more rings, the rings may be fused to each other.
  • C 2 -C 60 alkylheteroaryl group refers to a C 1 -C 60 heteroaryl group substituted with a C 1 -C 60 alkyl group.
  • C 6 -C 60 aryloxy group indicates —OA 102 (wherein A 102 is the C 6 -C 60 aryl group), a C 6 -C 60 arylthio group as used herein indicates —SA 103 (wherein A 103 is the C 6 -C 60 aryl group), and the term “C 7 -C 60 arylalkyl group” as used herein indicates —A 104 A 105 (wherein A 105 is the C 6 -C 59 aryl group and A 104 is the C 1 -C 54 alkylene group).
  • C 1 -C 60 heteroaryloxy group refers to —OA 106 (wherein A 106 is the C 2 -C 60 heteroaryl group), the term “C 1 -C 60 heteroarylthio group” as used herein indicates —SA 107 (wherein A 107 is the C 1 -C 60 heteroaryl group), and the term “C 2 -C 60 heteroarylalkyl group” as used herein refers to —A 108 A 109 (A 109 is a C 1 -C 59 heteroaryl group, and A 108 is a C 1 -C 59 alkylene group).
  • the term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and having no aromaticity in its entire molecular structure.
  • Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group.
  • divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
  • the term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, an N, O, P, Si, Se, S, or any combination thereof and carbon atoms, as ring-forming atoms, and no aromaticity in its entire molecular structure.
  • Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group.
  • divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
  • C 5 -C 30 carbocyclic group refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only.
  • the C 5 -C 30 carbocyclic group may be a monocyclic group or a polycyclic group.
  • C 2 -C 30 heterocyclic group refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, an N, O, Si, P, Se, S, or any combination thereof and 1 to 30 carbon atoms.
  • the C 2 -C 30 heterocyclic group may be a monocyclic group or a polycyclic group.
  • a deuterium —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group;
  • a CH 2 CN group is a C 1 group substituted with a nitrile.
  • Q 1 to Q 9 , Q 11 to Q 19 , Q 21 to Q 29 , and Q 31 to Q 39 in this disclosure may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C 1 -C 60 alkyl group unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a C 6 -C 60 aryl group, or any combination thereof; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; a C 3 -C 10 cycloalky
  • CBP and Compound 1 were co-deposited at a weight ratio of 9:1 at a vacuum pressure of 10 ⁇ 7 torr to manufacture a film having a thickness of 40 nanometers (nm).
  • a PLQY of the film was evaluated by using a Hamamatsu Photonics absolute PL quantum yield measurement system including a xenon light source, a monochromator, a photonic multichannel analyzer, an integrating sphere and employing a PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan), and a PLQY of Compound 1 was confirmed.
  • the results of this study are shown in Table 2.
  • TCSPC time-correlated single photon counting
  • T decay (Ex) (decay time) of the film was obtained by fitting one or more exponential decay functions to the result obtained therefrom, and the radiative decay rate that is a reciprocal of T decay (Ex) was calculated.
  • the results are shown in Table 2.
  • the function used for fitting is expressed by Equation 20, and the greatest value of T decay obtained from each exponential decay function used for fitting was taken as T decay (Ex).
  • a baseline or background signal curve was obtained by repeating the same measurement once more for the same measurement time as the measurement time for obtaining the TRPL curve in a dark state (a state in which a pumping signal applied to the predetermined film was blocked), and the baseline or background signal curve was used for fitting as a baseline.
  • mCP and Compound 1 were co-deposited on a fused silica base layer (thickness of 1 mm) at a weight ratio of 92:8 in a vacuum deposition apparatus having a vacuum pressure of 1 ⁇ 10 ⁇ 7 torr to form Sample 1 having a thickness of 30 nm (8 weight %), and Sample 1 was sealed with glass and glue in a nitrogen atmosphere. This procedure was repeated on Compounds shown in Table 3 to manufacture Samples 2 to 9.
  • each of Samples 1 to 8 was fixed on a semi-cylindrical lens, and a 325-nm laser was irradiated to emit light.
  • the emitted light passed through a polarization film, and p-polarization light emission strength was measured with respect to 530-nm light of 90° to 0° while turning by 1° with respect to the axis of the semi-cylindrical lens, to which the sample was fixed, by using a charge-coupled device (CCD).
  • CCD charge-coupled device
  • p-Polarization light emission strength (first p-polarization light emission strength) appearing when each Compound has a vertical orientation and p-polarization light emission strength (second p-polarization light emission strength) appearing when each Compound had a horizontal orientation were calculated with respect to 0° to 90°.
  • the weights at which p-polarization light emission strength were calculated by multiplying each weight by the first and second p-polarization light emission strengths coinciding with the measured p-polarization light emission strength, and the horizontal orientation ratios of Compounds shown in Table 3 were measured. The results of this study are shown in Table 3.
  • Table 3 The angle-dependent PL spectrum was analyzed by using a classical dipole moment regarded as dissipated power from a dipole oscillating light emission from excitons.
  • Compound 1 to 9 have excellent horizontal orientation ratios, that is, excellent horizontal optical orientation.
  • a glass substrate, on which ITO/Ag/ITO (70 ⁇ /1,000 ⁇ /70 ⁇ ) were deposited was cut to a size of 50 mm ⁇ 50 mm ⁇ 0.5 mm, sonicated with iso-propyl alcohol and pure water each for 5 minutes, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate was provided to a vacuum deposition apparatus.
  • 2-TNATA was vacuum-deposited on the anode of the glass substrate to form a hole injection layer having a thickness of 600 ⁇
  • a hole injection layer having a thickness of 600 ⁇
  • NPB 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl
  • CBP host
  • Compound 1 dopant
  • BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 ⁇
  • Alq 3 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 ⁇
  • LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 ⁇
  • MgAg was deposited on the electron injection layer at a weight ratio of 90:10 to form a cathode having a thickness of 120 ⁇ , thereby completing an organic light-emitting device having a structure of anode/2-TNATA (600 ⁇ )/NPB (1,350 ⁇ )/CBP+Compound 1 (6 weight %) (400 ⁇ )/BCP (50 ⁇ )/Alq 3 (350 ⁇ ) /LiF (10 ⁇ )/MgAg (120 ⁇ ).
  • Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compound shown in Table 4 were each used instead of Compound 1 as a dopant in forming an emission layer.
  • the driving voltage, current density, maximum quantum efficiency, roll-off ratio, full width at half maximum (FWHM), peak emission wavelength, and lifespan of the organic light-emitting devices manufactured according to Examples 1 to 9 and Comparative Example A to E were evaluated by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A), and results thereof are shown in Tables 4 and 5.
  • the roll-off ratio was calculated by Equation 30.
  • the lifespan (LT 99 , at 3,500 nit) indicates an amount of time that elapsed when luminance was 99% of initial luminance (100%) and is expressed by a relative value (%).
  • the organic light-emitting devices of Examples 1 to 9 have improved driving voltage, improved maximum quantum efficiency, and/or improved roll-off ratio, and also have improved lifespan characteristics, as compared with those of the organic light-emitting devices of Comparative Examples A to E.
  • the organometallic compound may emit light having a relatively small FWHM and have excellent PLQY, excellent radiative decay rate, and excellent horizontal orientation ratio
  • the organic light-emitting device including the organometallic compound may have improved driving voltage, external quantum efficiency, roll-off ratio, and lifespan characteristics.
  • a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

Abstract

An organometallic compound represented by Formula 1:
Figure US20200115406A1-20200416-C00001
    • wherein, in Formula 1, groups and variables are the same as described in the specification.

Description

    CROSS-REFERENCE TO RELATED APPLICATION
  • This application claims priority to Korean Patent Applications Nos. 10-2018-0104028, filed on Aug. 31, 2018, and 10-2019-0104976, filed on Aug. 27, 2019, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. § 119, the contents of which are incorporated herein in their entirety by reference.
    • BACKGROUND 1. Field
  • An embodiment relates to an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the organometallic compound.
    • 2. Description of the Related Art
  • Organic light-emitting devices (OLEDs) are self-emission devices, which have superior characteristics in terms of a viewing angle, a response time, a brightness, a driving voltage, and a response speed, and which produce full-color images.
  • In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.
  • Meanwhile, luminescent compounds may be used to monitor, sense, or detect a variety of biological materials including cells and proteins. An example of the luminescent compounds includes a phosphorescent luminescent compound.
  • Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.
    • SUMMARY
  • Aspects of the present disclosure provide an organometallic compound, an organic light-emitting device including the same, and a diagnostic composition including the organometallic compound.
  • Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.
  • An aspect of the present disclosure provides an organometallic compound represented by Formula 1:
  • Figure US20200115406A1-20200416-C00002
  • In Formula 1,
      • M may be a transition metal,
      • X1 may be O or S, wherein a bond between X1 and M may be a covalent bond,
      • X2 to X4 may each independently be C or N,
      • a bond between X2 and M, a bond between X3 and M, or a bond between X4 and M may be a covalent bond, and the other bonds of a bond between X2 and M, a bond between X3 and M, or a bond between X4 and M may be coordinate bonds,
      • Y1 and Y3 to Y5 may each independently be C or N,
      • a bond between X2 and Y3, a bond between X2 and Y4, and a bond between Y4 and Y5 may be a chemical bond, ring CY1 to ring CY4 and ring CY51 may each independently be a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
      • a cyclometalated ring formed by ring CY5, ring CY2, ring CY3, and M may be a 6-membered ring,
      • T1 may be a single bond, a double bond, *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═S)—*′, or *—C≡C—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
      • L1 to L4 and L51 may each independently be a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group, or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
      • b1 to b4 and b51 may each independently be an integer from 1 to 5,
      • R1 to R6, R51, and R52 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
      • c1 to c4, c51, and c52 may each independently be an integer from 1 to 5,
      • A51 may be a C4-C60 alkyl group,
      • A52 may be deuterium or a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group,
      • a1 to a4, a51, and a52 may each independently be an integer from 0 to 10, provided that the sum of a51 and a52 may be 1 or more,
      • a53 may be an integer from 1 to 10,
      • two or more groups of a plurality of R1 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
      • two or more groups of a plurality of R2 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
      • two or more groups of a plurality of R3 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
      • two or more groups of a plurality of R4 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
      • two or more groups of R1 to R6 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
      • R10a may be the same as described in connection with R1,
      • a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C2-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
      • a deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
      • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
      • a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
      • —N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
      • any combination thereof; and
      • Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C2-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C7-C60 arylalkyl group; a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group; a C1-C60 heteroarylthio group; a C2-C60 heteroarylalkyl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
  • Another aspect of the present disclosure provides an organic light-emitting device including:
      • a first electrode;
      • a second electrode; and
      • an organic layer disposed between the first electrode and the second electrode,
      • wherein the organic layer includes an emission layer and an organometallic compound represented by Formula 1.
  • The organometallic compound included in the emission layer in the organic layer may act as a dopant.
  • Another aspect of the present disclosure provides a diagnostic composition including an organometallic compound represented by Formula 1.
    • BRIEF DESCRIPTION OF THE DRAWING
  • These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the FIGURE which is a schematic view of an organic light-emitting device according to an embodiment.
    • DETAILED DESCRIPTION
  • Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
  • It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
  • It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.
  • The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
  • The term “or” means “and/or.” It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
  • Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
  • Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
  • “About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
  • In an embodiment, an organometallic compound is provided. The organometallic compound according to an embodiment may be represented by Formula 1:
  • Figure US20200115406A1-20200416-C00003
  • In Formula 1, M may be a transition metal. Alternatively, M may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au). For example, M may be Pt, Pd, or Au.
  • In Formula 1, X1 may be O or S, wherein a bond between X1 and M may be a covalent bond. For example, X1 may be O.
  • In Formula 1, X2 to X4 may each independently be C or N. For example, X2 and X3 may each independently be C or N, and X4 may be N.
  • In an embodiment, in Formula 1, X2 and X4 may each be N, and X3 may be C, but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, a bond between X2 and M, a bond between X3 and M, or a bond between X4 and M may be a covalent bond, and the other bonds of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M may be coordinate bonds. Therefore, the organometallic compound represented by Formula 1 may be electrically neutral.
  • In an embodiment, a bond between X2 and M and a bond between X4 and M may be a coordinate bond, and a bond between X3 and M may be a covalent bond, but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, Y1 and Y3 to Y5 may each independently be C or N. For example, Y1 and Y3 to Y5 may be C.
  • In Formula 1, a bond between X2 and Y3, a bond between X2 and Y4, and a bond between Y4 and Y5 may be a chemical bond (for example, a single bond, a double bond, or the like).
  • In Formula 1, ring CY1 to ring CY4 and ring CY51 may each independently be a C5-C30 carbocyclic group or a C2-C30 heterocyclic group.
  • For example, ring CY1 to ring CY4 and ring CY51 may each independently be i) a first ring, ii) a second ring, iii) a condensed ring in which at least two first rings are condensed, iv) a condensed ring in which at least two second rings are condensed, or v) a condensed ring in which a first ring and a second ring are condensed.
  • In an embodiment, the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzosilole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilole group, or a triazasilole group, and the second ring may be an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.
  • In an embodiment, in Formula 1, ring CY1 to ring CY4 and ring CY51 may each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.
  • In an embodiment, in Formula 1, ring CY4 may not be a benzimidazole group.
  • In Formula 1, a cyclometalated ring formed by ring CY5, ring CY2, ring CY3, and M may be a 6-membered ring.
  • In Formula 1, T1 may be a single bond, a double bond, *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═S)-, or *—C≡C—*′, wherein * and *′ each indicate a binding site to a neighboring atom. Here, R5 and R6 are the same as described above, and may optionally be linked to each other via a single bond, a double bond, *—N(R′)—*′, *—B(R′)—*′, *—P(R′)—*′, *—C(R′)(R″)—*′, *—Si(R′)(R″)—*′, *—Ge(R′)(R″)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*′, *—C(R′)=*′ *═C(R′)—*′, *—C(R′)═C(R″)—*′, *—C(═S)—*′, or *—C≡C—*′ to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group. R′, R″, and R10a are each independently defined the same as R1.
  • For example, in Formula 1, T1 may be a single bond, but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, L1 to L4 and L51 may each independently be a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group, or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group. Here, R10a is defined the same as R1.
  • For example, in Formula 1, L1 to L4 and L51 may each independently be:
      • a single bond; or
      • a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group, each unsubstituted or substituted with an R10a group.
  • In an embodiment, in Formula 1, L1 to L4 and L51 may each independently be:
      • a single bond; or
      • a benzene group unsubstituted or substituted with an R10a group,
      • but embodiments of the present disclosure are not limited thereto.
  • In an embodiment, in Formula 1,
  • Y1 and X3 may be C, and X2 and X4 may be N,
  • ring CY1 to ring CY3 and ring CY51 may be a benzene group, and ring CY4 may be a pyridine group, and
  • L4 and L51 may each independently be:
      • a single bond; or
      • a benzene group unsubstituted or substituted with an R10a group.
  • In Formula 1, b1 to b4 and b51 each indicate the number of L1 to L4 and L51, respectively, and may each independently be an integer from 1 to 5. When b1 is two or more, two or more L1 groups may be identical to or different from each other, when b2 is two or more, two or more L2 groups may be identical to or different from each other, when b3 is two or more, two or more L3 groups may be identical to or different from each other, when b4 is two or more, two or more L4 groups may be identical to or different from each other, and when b51 is two or more, two or more L51 groups may be identical to or different from each other.
  • For example, in Formula 1, b1 to b4 and b51 may each independently be 1, 2 or 3, but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, R1 to R6, R51, and R52 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), wherein Q1 to Q9 are each independently the same as described above.
  • For example, R1 to R6, R51, and R52 may each independently be:
      • a hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, C1-C20 alkyl group, or a C1-C20 alkoxy group;
      • a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl (adamantyl) group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group (for example, *—C(CD3)3), a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, or any combination thereof; or
      • —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9), and
      • Q1 to Q9 may each independently be:
      • —CH3, —CD3, —CD2H, —CDH2, —CH2CH3, —CH2CD3, —CH2CD2H, —CH2CDH2, —CHDCH3, —CHDCD2H, —CHDCDH2, —CHDCD3, —CD2CD3, —CD2CD2H, or —CD2CDH2; or
      • an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentyl group, a phenyl group, a biphenyl group or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof,
      • but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, c1 to c4, c51, and c52 each indicate the number of R1 to R4, R51, and R52, respectively, and may each independently be an integer from 1 to 5. When c1 is two or more, two or more R1 groups may be identical to or different from each other, when c2 is two or more, two or more R2 groups may be identical to or different from each other, when c3 is two or more, two or more R3 groups may be identical to or different from each other, when c4 is two or more, two or more R4 groups may be identical to or different from each other, when c51 is two or more, two or more R51 groups may be identical to or different from each other, and when c52 is two or more, two or more R52 groups may be identical to or different from each other. For example, c1 to c4, c51, and c52 may each independently be 1 or 2, but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, A51 may be a C4-C60 alkyl group, and A52 may be deuterium or a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group.
  • In an embodiment, in Formula 1, A51 may be a linear or branched C4-C10 alkyl group, and A52 may be deuterium or a deuterium-containing linear or branched C1-C20 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group.
  • In an embodiment, in Formula 1, A51 may be an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-iso-pentyl group, unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentyl group, or any combination thereof. For example, Formula 9-33 may be a branched C6 alkyl group and a tert-butyl group substituted with two methyl groups.
  • In an embodiment, in Formula 1, A52 may be a deuterium-containing linear or branched C1-C20 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, in which the linear or branched C1-C20 alkyl group may be a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-iso-pentyl group, unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentyl group, or any combination thereof.
  • The deuterium-containing C1-C60 alkyl group (or, the deuterium-containing C1-C20 alkyl group, the deuterium-containing C2-C20 alkyl group, etc.) means a C1-C60 alkyl group substituted with a deuterium (or, a C1-C20 alkyl group substituted with a deuterium, a C2-C20 alkyl group substituted with a deuterium, etc.). For example, a deuterium-containing C1 alkyl group (that is, a deuterium-containing methyl group) includes —CD3, —CD2H and —CDH2.
  • The deuterium-containing C1-C60 alkyl group (or, the deuterium-containing C1-C20 alkyl group, the deuterium-containing C2-C20 alkyl group, etc.) may be additionally substituted with a C3-C10 cycloalkyl group. For example, Formula 9-619 is a group corresponding to —CD2H, in which “—H” is substituted with a cyclopentyl group.
  • The organometallic compound represented by Formula 1 may include a deuterium, a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, or any combination thereof. The number of deuterium atoms in the organometallic compound represented by Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • In an embodiment, regarding Formula 1,
      • R1 to R6, R51, and R52 may each independently be:
      • hydrogen, deuterium, —F, a cyano group, a nitro group, —SF5, —CH3, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a group represented by one of Formulae 9-1 to 9-66, a group represented by one of Formulae 9-1 to 9-66 in which a hydrogen is substituted with deuterium, a group represented by one of Formulae 10-1 to 10-118, a group represented by one of Formulae 10-1 to 10-118 in which a hydrogen is substituted with deuterium, a group represented by one of Formulae 10-201 to 10-342, or a group represented by one of Formulae 10-201 to 10-342 in which a hydrogen is substituted with deuterium, and/or
      • A51 may be a group represented by one of Formulae 9-4 to 9-36, and/or
      • A52 may be a group represented by one of Formulae 9-1 to 9-63 in which a hydrogen is substituted with deuterium, and/or
      • a group represented by
  • Figure US20200115406A1-20200416-C00004
  • in Formula 1 may be a group represented by one of Formulae 10-10 to 10-118, or a group represented by one of Formulae 10-10 to 10-118 in which a hydrogen is substituted with deuterium:
  • Figure US20200115406A1-20200416-C00005
    Figure US20200115406A1-20200416-C00006
    Figure US20200115406A1-20200416-C00007
    Figure US20200115406A1-20200416-C00008
    Figure US20200115406A1-20200416-C00009
    Figure US20200115406A1-20200416-C00010
    Figure US20200115406A1-20200416-C00011
    Figure US20200115406A1-20200416-C00012
    Figure US20200115406A1-20200416-C00013
    Figure US20200115406A1-20200416-C00014
    Figure US20200115406A1-20200416-C00015
    Figure US20200115406A1-20200416-C00016
    Figure US20200115406A1-20200416-C00017
    Figure US20200115406A1-20200416-C00018
    Figure US20200115406A1-20200416-C00019
    Figure US20200115406A1-20200416-C00020
    Figure US20200115406A1-20200416-C00021
    Figure US20200115406A1-20200416-C00022
    Figure US20200115406A1-20200416-C00023
    Figure US20200115406A1-20200416-C00024
  • Figure US20200115406A1-20200416-C00025
    Figure US20200115406A1-20200416-C00026
    Figure US20200115406A1-20200416-C00027
    Figure US20200115406A1-20200416-C00028
    Figure US20200115406A1-20200416-C00029
    Figure US20200115406A1-20200416-C00030
    Figure US20200115406A1-20200416-C00031
    Figure US20200115406A1-20200416-C00032
    Figure US20200115406A1-20200416-C00033
    Figure US20200115406A1-20200416-C00034
    Figure US20200115406A1-20200416-C00035
    Figure US20200115406A1-20200416-C00036
    Figure US20200115406A1-20200416-C00037
    Figure US20200115406A1-20200416-C00038
    Figure US20200115406A1-20200416-C00039
  • In Formulae 9-1 to 9-66, 10-1 to 10-118 and 10-201 to 10-342, * indicates a binding site to a neighboring atom, Ph indicates a phenyl group, and TMS indicates a trimethylsilyl group.
  • The “group represented by one of Formulae 9-1 to 9-66 in which a hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 9-501 to 9-514 or 9-601 to 9-638.
  • Figure US20200115406A1-20200416-C00040
    Figure US20200115406A1-20200416-C00041
    Figure US20200115406A1-20200416-C00042
    Figure US20200115406A1-20200416-C00043
    Figure US20200115406A1-20200416-C00044
    Figure US20200115406A1-20200416-C00045
  • The “group represented by one of Formulae 10-1 to 10-118 in which a hydrogen is substituted with deuterium” may be, for example, a group represented by one of Formulae 10-501 to 10-552:
  • Figure US20200115406A1-20200416-C00046
    Figure US20200115406A1-20200416-C00047
    Figure US20200115406A1-20200416-C00048
    Figure US20200115406A1-20200416-C00049
    Figure US20200115406A1-20200416-C00050
    Figure US20200115406A1-20200416-C00051
  • In an embodiment, in Formula 1, A52 may be a group represented by one of Formulae 9-1 to 9-36 in which all hydrogens are substituted with deuterium, but embodiments of the present disclosure are not limited thereto.
  • In Formula 1, a1 to a4, a51, and a52 each indicate the number of *-[(L1)b1-(R1)c1], *-[(L2)b2-(R2)c2], *-[(L3)b3-(R3)c3], *-[(L4)b4-(R4)c4], A51, and A52, respectively, and may each independently be an integer from 0 to 10. When a1 is two or more, two or more *-[(L1)b1-(R1)c1] groups may be identical to or different from each other, when a2 is two or more, two or more *-[(L2)b2-(R2)c2] groups may be identical to or different from each other, when a3 is two or more, two or more *-[(L3)b3-(R3)c3] groups may be identical to or different from each other, when a4 is two or more, two or more *-[(L4)b4-(R4)c4] groups may be identical to or different from each other, when a51 is two or more, two or more A51 groups may be identical to or different from each other, and when a52 is two or more, two or more A52 groups may be identical to or different from each other, but embodiments of the present disclosure are not limited thereto.
  • For example, in Formula 1, a1 to a4, a51, and a52 may each independently be 0, 1, 2, 3, 4, 5, or 6, but embodiments of the present disclosure are not limited thereto.
  • For example, in Formula 1, a1 and a4 may each independently be 0, 1, 2, 3, or 4 and a2, a3, a51 and a52 may each independently be 0, 1, 2, or 3.
  • In Formula 1, the sum of a51 and a52 may be 1 or more. That is, in Formula 1, ring CY51 may be substituted with a group represented by A51, a group represented by A52, or any combination thereof.
  • For example, the sum of a51 and a52 may be 1, 2, or 3. In an embodiment, the sum of a51 and a52 may be 1 or 2.
  • In Formula 1, a53 indicates the number of groups represented by
  • Figure US20200115406A1-20200416-C00052
  • and may be an integer from 1 to 10. Since a53 in Formula 1 is not 0, ring CY51 in
  • Formula 1 is substituted with a group represented by
  • Figure US20200115406A1-20200416-C00053
  • In an embodiment, in Formula 1,
      • L1 to L3 may be a single bond, and
      • R1 to R3 may each independently be:
      • hydrogen, deuterium, —F, a cyano group, C1-C20 alkyl group, or a C1-C20 alkoxy group;
      • a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof; or
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group (for example, *—C(CD3)3), a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
  • In an embodiment, in Formula 1, a3, and a4 may not be 0, and a group represented by *-(L3)b3-(R3)c3, and a group represented by *-(L4)b4-(R4)c4 may not be hydrogen.
  • In an embodiment, in Formula 1, a1, a3, and a4 may not be 0, and a group represented by *-(L1)b1-(R1)c1, a group represented by *-(L3)b3-(R3)c3, and a group represented by *-(L4)b4-(R4)c4 may not be hydrogen.
  • In an embodiment, in Formula 1, a1 may not be 0, a group represented by *-(L1)b1-(R1)c1 may not be hydrogen, and a group represented by *-(L1)b1-(R1)c1 in a number of a1 may include a deuterium.
  • In an embodiment, in Formula 1, a1 may be 2, two groups represented by *-(L1)b1-(R1)c1 may not be hydrogen, and two groups represented by *-(L1)b1-(R1)c1 may be identical to each other.
  • In an embodiment, in Formula 1, a1 may be 2, two groups represented by *-(L1)b1-(R1)c1 may not be hydrogen, and two groups represented by *-(L1)b1-(R1)c1 may be different from each other.
  • In an embodiment, in Formula 1, a4 may not be 0, a group represented by *-(L4)b4-(R4)c4 may not be hydrogen, and a group represented by *-(L4)b4-(R4)c4 in a number of a4 may include a deuterium.
  • In an embodiment, in Formula 1, a3 may not be 0, and a group represented by *-(L3)b3-(R3)c3 in a number of a3 may satisfy Condition A and Condition B:
      • Condition A
      • L3 is a single bond.
      • Condition B
      • R3 is
      • hydrogen, deuterium, —F, a cyano group, C1-C20 alkyl group, or a C1-C20 alkoxy group;
      • a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof; or
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
  • In an embodiment, in Condition B, R3 may not hydrogen.
  • In an embodiment, in Formula 1, a3 may not be 0, and a group represented by *-(L3)b3-(R3)c3 in a number of a3 may satisfy Condition A and Condition B(1):
      • Condition A
      • L3 is a single bond.
      • Condition B(1)
      • R3 is
      • a C4-C20 alkyl group unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof; or
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
  • In an embodiment, in Formula 1, a4 may not be 0, and a group represented by *-(L4)b4-(R4)c4 in a number of a4 may satisfy Condition 1, Condition 2, or combination thereof:
      • Condition 1
      • R4 in a number of c4 is a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.
      • Condition 2
      • L4 is not a single bond.
  • In an embodiment, in Formula 1, a4 may not be 0, and a group represented by *-(L4)b4-(R4)c4 in a number of a4 may satisfy Condition 1(1), Condition 2(1), or combination thereof:
      • Condition 1(1)
      • R4 in a number of c4 is a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
      • Condition 2(1)
      • L4 is a benzene group unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
  • In an embodiment, in Formula 1, a4 may not be 0, and a group represented by *-(L4)b4-(R4)c4 in a number of a4 may satisfy Condition 3, Condition 4, Condition 5, or combination thereof:
      • Condition 3
      • R4 in a number of c4 is a substituted C6-C60 aryl group.
      • Condition 4
      • L4 is a C5-C30 carbocyclic group substituted with an R10a group,
      • Condition 5
      • L4 is a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group and R4 is not hydrogen.
  • In an embodiment, in Formula 1, a4 may not be 0, and a group represented by *-(L4)b4-(R4)c4 in a number of a4 may satisfy Condition 3(1), Condition 4(1), Condition 5(1), or combination thereof:
      • Condition 3(1)
      • R4 in a number of c4 is a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
      • Condition 4(1)
      • L4 is a benzene group substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
      • Condition 5(1)
      • L4 is a benzene group unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof, and
      • R4 is
      • deuterium, —F, a cyano group, C1-C20 alkyl group, or a C1-C20 alkoxy group;
      • a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof; or
      • a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
  • In an embodiment, in Formula 1, a51 and a52 may each independently be 0, 1 or 2, the sum of a51 and a52 may be 1 or 2, and a53 may be 1 or 2.
  • * and *′ each indicate a binding site to a neighboring atom.
  • For example, a group represented by
  • Figure US20200115406A1-20200416-C00054
  • in Formula 1 may be a group represented by one of Formulae A1(1) to A1(30):
  • Figure US20200115406A1-20200416-C00055
    Figure US20200115406A1-20200416-C00056
    Figure US20200115406A1-20200416-C00057
    Figure US20200115406A1-20200416-C00058
  • In Formulae A1(1) to A1(30),
      • Y1, L1, b1, R1, and c1 may each independently be the same as described herein,
      • X11 may be O, S, N(R11), C(R11)(R12), or Si(R11)(R12),
      • R11 to R18 may each independently be the same as described in connection with R1,
      • a12 may be an integer from 0 to 2,
      • a13 may be an integer from 0 to 3,
      • a14 may be an integer from 0 to 4,
      • a15 may be an integer from 0 to 5,
      • a16 may be an integer from 0 to 6,
      • *′ indicates a binding site to X1 in Formula 1, and
      • indicates a binding site to Y3 in Formula 1.
  • The group represented by
  • Figure US20200115406A1-20200416-C00059
  • in Formula 1 may include deuterium, a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, or any combination thereof. The number of deuterium atoms in the group represented by
  • Figure US20200115406A1-20200416-C00060
  • in Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • In an embodiment, a group represented by
  • Figure US20200115406A1-20200416-C00061
  • in Formula 1 may be a group represented by one of Formulae A2(1) to A2(4):
  • Figure US20200115406A1-20200416-C00062
  • In Formulae A2(1) to A2(4),
      • X2, L2, b2, R2, and c2 may each independently be the same as described herein,
      • a22 may be an integer from 0 to 2,
      • a23 may be an integer from 0 to 3,
      • Figure US20200115406A1-20200416-P00001
        indicates a binding site to L51 in Formula 1,
      • *″ indicates a binding site to ring CY3 in Formula 1,
      • *′ indicates a binding site to M in Formula 1, and
      • * indicates a binding site to ring CY1 in Formula 1.
  • The group represented by
  • Figure US20200115406A1-20200416-C00063
  • in Formula 1 may include deuterium, a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, or any combination thereof. The number of deuterium atoms in the group represented by
  • Figure US20200115406A1-20200416-C00064
  • in Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • In an embodiment, a group represented by
  • Figure US20200115406A1-20200416-C00065
  • in Formula 1 may be a group represented by one of Formulae A3(1) to A3(17):
  • Figure US20200115406A1-20200416-C00066
    Figure US20200115406A1-20200416-C00067
    Figure US20200115406A1-20200416-C00068
  • In Formulae A3(1) to A3(17),
      • X3, L3, b3, R3, and c3 may each independently be the same as described herein,
      • X31 may be O, S, N(R31), C(R31)(R32), or Si(R31)(R32),
      • R31 to R38 may each independently be the same as described in connection with
      • a32 may be an integer from 0 to 2,
      • a33 may be an integer from 0 to 3,
      • a34 may be an integer from 0 to 4,
      • a35 may be an integer from 0 to 5,
      • *″ indicates a binding site to ring CY2 in Formula 1,
      • *′ indicates a binding site to M in Formula 1, and
      • indicates a binding site to T1 in Formula 1.
  • The group represented by
  • Figure US20200115406A1-20200416-C00069
  • in Formula 1 may include deuterium, a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, or any combination thereof. The number of deuterium atoms in the group represented by
  • Figure US20200115406A1-20200416-C00070
  • in Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • In an embodiment, a group represented by
  • Figure US20200115406A1-20200416-C00071
  • in Formula 1 may be a group represented by one of Formulae A4(1) to A4(45):
  • Figure US20200115406A1-20200416-C00072
    Figure US20200115406A1-20200416-C00073
    Figure US20200115406A1-20200416-C00074
    Figure US20200115406A1-20200416-C00075
    Figure US20200115406A1-20200416-C00076
    Figure US20200115406A1-20200416-C00077
    Figure US20200115406A1-20200416-C00078
  • In Formulae A4(1) to A4(45),
      • X4, L4, b4, R4, and c4 may each independently be the same as described herein,
      • X41 may be O, S, N(R41), C(R41)(R42), or Si(R41)(R42),
      • R41 to R48 may each independently be the same as described in connection with R4,
      • a42 may be an integer from 0 to 2,
      • a43 may be an integer from 0 to 3,
      • a44 may be an integer from 0 to 4,
      • a45 may be an integer from 0 to 5,
      • a46 may be an integer from 0 to 6,
      • *′ indicates a binding site to M in Formula 1, and
      • indicates a binding site to T1 in Formula 1.
  • The group represented by
  • Figure US20200115406A1-20200416-C00079
  • in Formula 1 may include deuterium, a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, or any combination thereof. The number of deuterium atoms in the group represented by
  • Figure US20200115406A1-20200416-C00080
  • in Formula 1 may be from 1 to 20, for example, from 1 to 15, from 1 to 10, or from 1 to 5.
  • In an embodiment, in Formula 1, a group represented by
  • Figure US20200115406A1-20200416-C00081
  • may be a group represented by one of Formulae CY1(1) to CY1(8), and/or
      • a group represented by
  • Figure US20200115406A1-20200416-C00082
  • may be a group represented by one of Formulae CY2(1) to CY2(4), and/or
      • a group represented by
  • Figure US20200115406A1-20200416-C00083
  • may be a group represented by one of Formulae CY3(1) to CY3(24), and/or
      • a group represented by
  • Figure US20200115406A1-20200416-C00084
  • may be a group represented by one of Formulae CY4(1) to CY4(74), but embodiments of the present disclosure are not limited thereto:
  • Figure US20200115406A1-20200416-C00085
    Figure US20200115406A1-20200416-C00086
    Figure US20200115406A1-20200416-C00087
    Figure US20200115406A1-20200416-C00088
    Figure US20200115406A1-20200416-C00089
    Figure US20200115406A1-20200416-C00090
    Figure US20200115406A1-20200416-C00091
    Figure US20200115406A1-20200416-C00092
    Figure US20200115406A1-20200416-C00093
    Figure US20200115406A1-20200416-C00094
    Figure US20200115406A1-20200416-C00095
    Figure US20200115406A1-20200416-C00096
    Figure US20200115406A1-20200416-C00097
    Figure US20200115406A1-20200416-C00098
  • In Formulae CY1(1) to CY1(8), CY2(1) to CY2(4), CY3(1) to CY3(24), and CY4(1) to CY4(74),
      • X2 to X4, Y1, L1 to L4, b1 to b4, R1 to R4, and c1 to c4 may each independently be the same as described herein,
      • X31 may be O, S, N(R31), C(R31)(R32), or Si(R31)(R32),
      • X41 may be O, S, N(R41), C(R41)(R42), or Si(R41)(R42),
      • L1a and L1b may each independently be the same as described in connection with L1,
      • R1a and R1b may each independently be the same as described in connection with R1,
      • L3a and L3b may each independently be the same as described in connection with L3,
      • R3a, R3b, R31, and R32 may each independently be the same as described in connection with R3,
      • L4a to L4d may each independently be the same as described in connection with L4,
      • R4a to R4d, R41, and R42 may each independently be the same as described in connection with R4,
      • *-(L1)b1-(R1)c1, *-(L1a)b1-(R1a)c1, *-(L1b)b1-(R1a)c1, *-(L2)b2-(R2)c2, *-(L3)b3-(R3)c3, * (L3a)b3-(R3a)c3, *-(L3b)b3-(R3a)c3, *-(L4)b4-(R4)c4, *-(L4a)b4-(R4a)c4, *-(L4b)b4-(R4a)c4, *-(L4c)b4-(R4c)c4, and *-(L4d)b4-(R4d)c4 may not be hydrogen, and * indicates a binding site to a neighboring atom,
      • in Formulae CY1(1) to CY1(8), *′ indicates a binding site to X1 in Formula 1,
      • in Formulae CY2(1) to CY2(4), CY3(1) to CY3(24), and CY4(1) to CY4(74), *′ indicates a binding site to M in Formula 1,
      • in Formulae CY1(1) to CY1(8), * indicates a binding site to Y3 in Formula 1,
      • in Formulae CY2(1) to CY2(4), * indicates a binding site to ring CY1 in Formula 1, and *″ indicates a binding site to ring CY3 in Formula 1,
      • in Formulae CY3(1) to CY3(24), *″ indicates a binding site to ring CY2 in Formula 1, and * indicates a binding site to T1 in Formula 1, and
      • in Formulae CY4(1) to CY4(74), * indicates a binding site to T1 in Formula 1.
  • In an embodiment, a group represented by
  • Figure US20200115406A1-20200416-C00099
  • may be a group represented by Formula CY4-1 or CY4-2:
  • Figure US20200115406A1-20200416-C00100
      • in Formulae CY4-1 and CY4-2,
      • X4, L4, b4, R4, and c4 may each independently be the same as described herein,
      • Z41 to Z44 may each independently be the same as described in connection with R4 herein,
      • *′ indicates a binding site to M in Formula 1, and
      • indicates a binding site to T1 in Formula 1.
  • For example, Formulae CY4-1 and CY4-2 may satisfy:
  • 1) Condition 1, Condition 2, or any combination thereof (or, Condition 1(1), Condition 2(1), or any combination thereof), and/or
  • 2) Condition 3, Condition 4, Condition 5, or any combination thereof (or, Condition 3(1), Condition 4(1), Condition 5(1), or any combination thereof).
  • In an embodiment, in Formula 1, a group represented by
  • Figure US20200115406A1-20200416-C00101
  • may be a group represented by Formula CY1(1) or CY1(6), and/or
  • a group represented by
  • Figure US20200115406A1-20200416-C00102
  • may be a group represented by Formula CY2(1), and/or
  • a group represented by
  • Figure US20200115406A1-20200416-C00103
  • may be a group represented by Formula CY3(3), and/or
    a group represented by
  • Figure US20200115406A1-20200416-C00104
  • may be a group represented by Formula CY4(3), CY4(4) or CY4(16).
  • In an embodiment, a group represented by
  • Figure US20200115406A1-20200416-C00105
  • in Formula 1 may be a group represented by one of Formulae 51-1 to 51-32:
  • Figure US20200115406A1-20200416-C00106
    Figure US20200115406A1-20200416-C00107
    Figure US20200115406A1-20200416-C00108
    Figure US20200115406A1-20200416-C00109
    Figure US20200115406A1-20200416-C00110
  • In Formulae 51-1 to 51-32, R51, R52, c52, A51, and A52 may each independently be the same as described herein, R53 and c53 may each independently be the same as described in connection with R52 and c52, c512 is an integer of 0 to 2, c513 is an integer of 0 to 3, and * indicates a binding site to L51.
  • In an embodiment, the organometallic compound may be represented by Formula 1-1 or 1-2:
  • Figure US20200115406A1-20200416-C00111
  • in Formulae 1-1 and 1-2,
  • M, X1 to X4, Y1, Y3 to Y5, L4, L51, b4, b51, R51, R52, c51, c52, A51, A52, a51, a52 and a53 may each independently be the same as described herein,
  • Z11 to Z14 may each independently be the same as described in connection with R1,
  • Z21 to Z23 may each independently be the same as described in connection with R2,
  • Z31 to Z33 may each independently be the same as described in connection with R3,
  • Z41 to Z44 may each independently be the same as described in connection with R4,
  • two or more groups of Z11 to Z14 may be optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
  • two or more groups of Z21 to Z23 may be optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
  • two or more groups of Z31 to Z33 may be optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
  • two or more groups of Z41 to Z44 may be optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group, and
  • R10a is the same as described in connection with R1.
  • Descriptions for Formula 1 described herein can be applied for Formulae 1-1 and 1-2.
  • For example,
  • 1) Formulae 1-1 and 1-2 may satisfy Condition A, Condition B, or any combination thereof (or, Condition A, Condition B(1), or any combination thereof), and/or
  • 2) Formulae 1-1 and 1-2 may satisfy Condition 1, Condition 2, or any combination thereof (or, Condition 1(1), Condition 2(1), or any combination thereof), and/or
  • 3) Formulae 1-1 and 1-2 may satisfy Condition 3, Condition 4, Condition 5, or any combination thereof (or, Condition 3(1), Condition 4(1), Condition 5(1), or any combination thereof), and/or
  • 4) a group represented by
  • Figure US20200115406A1-20200416-C00112
  • in Formulae 1-1 and 1-2 may be a group represented by one of Formulae 51-1 to 51-32.
  • In an embodiment, Z12, Z14, Z21 to Z23, Z31, Z33 and Z41 to Z44 in Formulae 1-1 and 1-2 may each independently be hydrogen, deuterium, —CH3, or —CD3.
  • In an embodiment, Z12, Z14, Z21 to Z23, Z31, Z33 and Z41 to Z44 in Formulae 1-1 and 1-2 may each independently be hydrogen, or deuterium.
  • In an embodiment, Z11 and Z13 in Formulae 1-1 and 1-2 may not be hydrogen and Z11 and Z13 may include a deuterium.
  • In an embodiment, Z11 and Z13 in Formulae 1-1 and 1-2 may not be hydrogen and Z11 and Z13 may be identical to each other.
  • In an embodiment, Z11 and Z13 in Formulae 1-1 and 1-2 may not be hydrogen and Z11 and Z13 may be different from each other.
  • In Formula 1, i) two or more groups of a plurality of R1 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group, ii) two or more groups of a plurality of R2 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group, iii) two or more groups of a plurality of R3 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group, iv) two or more groups of a plurality of R4 groups may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group, and v) two or more groups of R1 to R6 may optionally be linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group. An R10a group may be the same as described in connection with R1.
  • For example, a C5-C30 carbocyclic group (that is unsubstituted or substituted with an R10a group) and a C2-C30 heterocyclic group (that is unsubstituted or substituted with an R10a group) may each independently be a cyclopentane group, a silole group, an azasilole group, a diazasilole group, a triazasilole group, an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.1]heptane group, a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene-5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group, each unsubstituted or substituted with an R1a group, but embodiments of the present disclosure are not limited thereto.
  • Non-limiting examples of the C1-C60 alkyl group, C1-C20 alkyl group and/or C1-C10 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, or a tert-decyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof, and the like, but embodiments of the present disclosure are not limited thereto.
  • Non-limiting examples of the C1-C60 alkoxy group, C1-C20 alkoxy group and/or C1-C10 alkoxy group include a methoxy group, an ethoxy group, a propoxy group or a butoxy group, and the like, but embodiments of the present disclosure are not limited thereto.
  • Non-limiting examples of the C3-C10 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, and the like, but embodiments of the present disclosure are not limited thereto.
  • An angle formed by a plane including the transition dipole moment of the organometallic compound represented by Formula 1 and a plane including four atoms of a tetradentate ligand linked to a metal M of Formula 1 may be about 10° or less. In addition, a horizontal orientation ratio of the transition dipole moment of the organometallic compound represented by Formula 1 may be in a range of about 80% to about 100%.
  • For example, the angle formed by the plane including the transition dipole moment of the organometallic compound and the plane including the four atoms of the tetradentate ligand linked to the metal (or platinum) of Formula 1 may be 0° to 10°, 0° to 9°, 0° to 8°, 0° to 7°, 0° to 6°, 0° to 5°, 0° to 4°, 0° to 3°, 0° to 2°, or 0° to 1°, but embodiments of the present disclosure are not limited thereto. When the angle formed by the plane including the transition dipole moment of the organometallic compound represented by the Formula 1 and the plane including the four atoms of the tetradentate ligand linked to the metal of Formula 1 is within these ranges, the organometallic compound may have excellent planarity, and a thin film formed by using the organometallic compound may have excellent electric characteristics.
  • In an embodiment, the horizontal orientation ratio of the transition dipole moment of the organometallic compound may be in a range of, for example, 80% to 100%, 81% to 100%, 82% to 100%, 83% to 100%, 84% to 100%, 85% to 100%, 86% to 100%, 87% to 100%, 88% to 100%, 89% to 100%, 90% to 100%, 91% to 100%, 92% to 100%, 93% to 100%, 94% to 100%, 95% to 100%, 96% to 100%, 97% to 100%, 98% to 100%, 99% to 100%, or 100%, but embodiments of the present disclosure are not limited thereto.
  • The horizontal orientation ratio of the transition dipole moment means a ratio of the organometallic compound having a transition dipole moment horizontal to the film including the organometallic compound to the total organometallic compound in the film including the organometallic compound.
  • The horizontal orientation ratio of the transition dipole moment may be evaluated by using an angle-dependent PL measurement apparatus. The angle-dependent PL measurement apparatus may be understood by referring to Korean Patent Application No. 10-2013-0150834, the content of which is incorporated herein in its entirety by reference.
  • Since the organometallic compound has a high horizontal orientation ratio of a transition dipole moment, the organometallic compound has a large horizontal orientation transition dipole moment (that is, a large horizontal optical orientation). Therefore, a large amount of electric field traveling in a direction perpendicular to the film including the organometallic compound may be emitted. Light emitted due to such a mechanism may have high external extraction efficiency (that is, efficiency of extracting light emitted in the organometallic compound from a device (for example, an organic light-emitting device) including a film (for example, an emission layer described below) including the organometallic compound) to the outside, and thus, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound, may have high luminescent efficiency.
  • The terms “an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, and an azadibenzothiophene 5,5-dioxide group” as used herein each refer to a heterocyclic group having the same backbone as that of each of “an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, and a dibenzothiophene 5,5-dioxide group”, respectively, wherein an ring-forming carbons of the rings above is substituted with nitrogen.
  • In addition, R10a is defined the same as R1.
  • For example, the organometallic compound represented by Formula 1 may include a deuterium.
  • In an embodiment, the organometallic compound may be one of the following Compounds 1 to 3599:
  • Figure US20200115406A1-20200416-C00113
    Figure US20200115406A1-20200416-C00114
    Figure US20200115406A1-20200416-C00115
    Figure US20200115406A1-20200416-C00116
    Figure US20200115406A1-20200416-C00117
    Figure US20200115406A1-20200416-C00118
    Figure US20200115406A1-20200416-C00119
    Figure US20200115406A1-20200416-C00120
    Figure US20200115406A1-20200416-C00121
    Figure US20200115406A1-20200416-C00122
    Figure US20200115406A1-20200416-C00123
    Figure US20200115406A1-20200416-C00124
    Figure US20200115406A1-20200416-C00125
    Figure US20200115406A1-20200416-C00126
    Figure US20200115406A1-20200416-C00127
    Figure US20200115406A1-20200416-C00128
    Figure US20200115406A1-20200416-C00129
    Figure US20200115406A1-20200416-C00130
    Figure US20200115406A1-20200416-C00131
    Figure US20200115406A1-20200416-C00132
    Figure US20200115406A1-20200416-C00133
    Figure US20200115406A1-20200416-C00134
    Figure US20200115406A1-20200416-C00135
    Figure US20200115406A1-20200416-C00136
    Figure US20200115406A1-20200416-C00137
    Figure US20200115406A1-20200416-C00138
    Figure US20200115406A1-20200416-C00139
    Figure US20200115406A1-20200416-C00140
    Figure US20200115406A1-20200416-C00141
    Figure US20200115406A1-20200416-C00142
    Figure US20200115406A1-20200416-C00143
    Figure US20200115406A1-20200416-C00144
    Figure US20200115406A1-20200416-C00145
    Figure US20200115406A1-20200416-C00146
    Figure US20200115406A1-20200416-C00147
    Figure US20200115406A1-20200416-C00148
    Figure US20200115406A1-20200416-C00149
    Figure US20200115406A1-20200416-C00150
    Figure US20200115406A1-20200416-C00151
    Figure US20200115406A1-20200416-C00152
    Figure US20200115406A1-20200416-C00153
    Figure US20200115406A1-20200416-C00154
    Figure US20200115406A1-20200416-C00155
    Figure US20200115406A1-20200416-C00156
    Figure US20200115406A1-20200416-C00157
    Figure US20200115406A1-20200416-C00158
    Figure US20200115406A1-20200416-C00159
  • Figure US20200115406A1-20200416-C00160
    Figure US20200115406A1-20200416-C00161
    Figure US20200115406A1-20200416-C00162
    Figure US20200115406A1-20200416-C00163
    Figure US20200115406A1-20200416-C00164
    Figure US20200115406A1-20200416-C00165
    Figure US20200115406A1-20200416-C00166
    Figure US20200115406A1-20200416-C00167
    Figure US20200115406A1-20200416-C00168
    Figure US20200115406A1-20200416-C00169
    Figure US20200115406A1-20200416-C00170
    Figure US20200115406A1-20200416-C00171
    Figure US20200115406A1-20200416-C00172
    Figure US20200115406A1-20200416-C00173
    Figure US20200115406A1-20200416-C00174
    Figure US20200115406A1-20200416-C00175
    Figure US20200115406A1-20200416-C00176
    Figure US20200115406A1-20200416-C00177
    Figure US20200115406A1-20200416-C00178
    Figure US20200115406A1-20200416-C00179
    Figure US20200115406A1-20200416-C00180
    Figure US20200115406A1-20200416-C00181
    Figure US20200115406A1-20200416-C00182
    Figure US20200115406A1-20200416-C00183
    Figure US20200115406A1-20200416-C00184
    Figure US20200115406A1-20200416-C00185
    Figure US20200115406A1-20200416-C00186
  • Figure US20200115406A1-20200416-C00187
    Figure US20200115406A1-20200416-C00188
    Figure US20200115406A1-20200416-C00189
    Figure US20200115406A1-20200416-C00190
    Figure US20200115406A1-20200416-C00191
    Figure US20200115406A1-20200416-C00192
    Figure US20200115406A1-20200416-C00193
    Figure US20200115406A1-20200416-C00194
    Figure US20200115406A1-20200416-C00195
    Figure US20200115406A1-20200416-C00196
    Figure US20200115406A1-20200416-C00197
    Figure US20200115406A1-20200416-C00198
    Figure US20200115406A1-20200416-C00199
    Figure US20200115406A1-20200416-C00200
    Figure US20200115406A1-20200416-C00201
    Figure US20200115406A1-20200416-C00202
    Figure US20200115406A1-20200416-C00203
    Figure US20200115406A1-20200416-C00204
    Figure US20200115406A1-20200416-C00205
    Figure US20200115406A1-20200416-C00206
    Figure US20200115406A1-20200416-C00207
    Figure US20200115406A1-20200416-C00208
    Figure US20200115406A1-20200416-C00209
    Figure US20200115406A1-20200416-C00210
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    Figure US20200115406A1-20200416-C00637
    Figure US20200115406A1-20200416-C00638
    Figure US20200115406A1-20200416-C00639
    Figure US20200115406A1-20200416-C00640
    Figure US20200115406A1-20200416-C00641
    Figure US20200115406A1-20200416-C00642
    Figure US20200115406A1-20200416-C00643
    Figure US20200115406A1-20200416-C00644
    Figure US20200115406A1-20200416-C00645
    Figure US20200115406A1-20200416-C00646
    Figure US20200115406A1-20200416-C00647
    Figure US20200115406A1-20200416-C00648
    Figure US20200115406A1-20200416-C00649
    Figure US20200115406A1-20200416-C00650
    Figure US20200115406A1-20200416-C00651
    Figure US20200115406A1-20200416-C00652
  • Figure US20200115406A1-20200416-C00653
    Figure US20200115406A1-20200416-C00654
    Figure US20200115406A1-20200416-C00655
    Figure US20200115406A1-20200416-C00656
    Figure US20200115406A1-20200416-C00657
    Figure US20200115406A1-20200416-C00658
    Figure US20200115406A1-20200416-C00659
    Figure US20200115406A1-20200416-C00660
    Figure US20200115406A1-20200416-C00661
    Figure US20200115406A1-20200416-C00662
    Figure US20200115406A1-20200416-C00663
    Figure US20200115406A1-20200416-C00664
    Figure US20200115406A1-20200416-C00665
    Figure US20200115406A1-20200416-C00666
    Figure US20200115406A1-20200416-C00667
    Figure US20200115406A1-20200416-C00668
    Figure US20200115406A1-20200416-C00669
    Figure US20200115406A1-20200416-C00670
    Figure US20200115406A1-20200416-C00671
    Figure US20200115406A1-20200416-C00672
    Figure US20200115406A1-20200416-C00673
    Figure US20200115406A1-20200416-C00674
    Figure US20200115406A1-20200416-C00675
    Figure US20200115406A1-20200416-C00676
    Figure US20200115406A1-20200416-C00677
    Figure US20200115406A1-20200416-C00678
    Figure US20200115406A1-20200416-C00679
    Figure US20200115406A1-20200416-C00680
    Figure US20200115406A1-20200416-C00681
    Figure US20200115406A1-20200416-C00682
    Figure US20200115406A1-20200416-C00683
    Figure US20200115406A1-20200416-C00684
    Figure US20200115406A1-20200416-C00685
    Figure US20200115406A1-20200416-C00686
    Figure US20200115406A1-20200416-C00687
    Figure US20200115406A1-20200416-C00688
    Figure US20200115406A1-20200416-C00689
    Figure US20200115406A1-20200416-C00690
  • Figure US20200115406A1-20200416-C00691
    Figure US20200115406A1-20200416-C00692
    Figure US20200115406A1-20200416-C00693
    Figure US20200115406A1-20200416-C00694
    Figure US20200115406A1-20200416-C00695
    Figure US20200115406A1-20200416-C00696
    Figure US20200115406A1-20200416-C00697
    Figure US20200115406A1-20200416-C00698
    Figure US20200115406A1-20200416-C00699
    Figure US20200115406A1-20200416-C00700
    Figure US20200115406A1-20200416-C00701
    Figure US20200115406A1-20200416-C00702
    Figure US20200115406A1-20200416-C00703
    Figure US20200115406A1-20200416-C00704
    Figure US20200115406A1-20200416-C00705
    Figure US20200115406A1-20200416-C00706
    Figure US20200115406A1-20200416-C00707
    Figure US20200115406A1-20200416-C00708
    Figure US20200115406A1-20200416-C00709
    Figure US20200115406A1-20200416-C00710
    Figure US20200115406A1-20200416-C00711
    Figure US20200115406A1-20200416-C00712
    Figure US20200115406A1-20200416-C00713
    Figure US20200115406A1-20200416-C00714
    Figure US20200115406A1-20200416-C00715
    Figure US20200115406A1-20200416-C00716
    Figure US20200115406A1-20200416-C00717
    Figure US20200115406A1-20200416-C00718
    Figure US20200115406A1-20200416-C00719
    Figure US20200115406A1-20200416-C00720
  • Figure US20200115406A1-20200416-C00721
    Figure US20200115406A1-20200416-C00722
    Figure US20200115406A1-20200416-C00723
    Figure US20200115406A1-20200416-C00724
    Figure US20200115406A1-20200416-C00725
    Figure US20200115406A1-20200416-C00726
    Figure US20200115406A1-20200416-C00727
    Figure US20200115406A1-20200416-C00728
    Figure US20200115406A1-20200416-C00729
    Figure US20200115406A1-20200416-C00730
    Figure US20200115406A1-20200416-C00731
    Figure US20200115406A1-20200416-C00732
    Figure US20200115406A1-20200416-C00733
    Figure US20200115406A1-20200416-C00734
    Figure US20200115406A1-20200416-C00735
    Figure US20200115406A1-20200416-C00736
    Figure US20200115406A1-20200416-C00737
    Figure US20200115406A1-20200416-C00738
    Figure US20200115406A1-20200416-C00739
    Figure US20200115406A1-20200416-C00740
    Figure US20200115406A1-20200416-C00741
    Figure US20200115406A1-20200416-C00742
    Figure US20200115406A1-20200416-C00743
    Figure US20200115406A1-20200416-C00744
    Figure US20200115406A1-20200416-C00745
    Figure US20200115406A1-20200416-C00746
    Figure US20200115406A1-20200416-C00747
    Figure US20200115406A1-20200416-C00748
    Figure US20200115406A1-20200416-C00749
    Figure US20200115406A1-20200416-C00750
    Figure US20200115406A1-20200416-C00751
    Figure US20200115406A1-20200416-C00752
    Figure US20200115406A1-20200416-C00753
    Figure US20200115406A1-20200416-C00754
    Figure US20200115406A1-20200416-C00755
    Figure US20200115406A1-20200416-C00756
    Figure US20200115406A1-20200416-C00757
    Figure US20200115406A1-20200416-C00758
    Figure US20200115406A1-20200416-C00759
    Figure US20200115406A1-20200416-C00760
    Figure US20200115406A1-20200416-C00761
    Figure US20200115406A1-20200416-C00762
    Figure US20200115406A1-20200416-C00763
    Figure US20200115406A1-20200416-C00764
    Figure US20200115406A1-20200416-C00765
    Figure US20200115406A1-20200416-C00766
    Figure US20200115406A1-20200416-C00767
    Figure US20200115406A1-20200416-C00768
    Figure US20200115406A1-20200416-C00769
    Figure US20200115406A1-20200416-C00770
  • Figure US20200115406A1-20200416-C00771
    Figure US20200115406A1-20200416-C00772
    Figure US20200115406A1-20200416-C00773
    Figure US20200115406A1-20200416-C00774
    Figure US20200115406A1-20200416-C00775
    Figure US20200115406A1-20200416-C00776
    Figure US20200115406A1-20200416-C00777
    Figure US20200115406A1-20200416-C00778
    Figure US20200115406A1-20200416-C00779
    Figure US20200115406A1-20200416-C00780
    Figure US20200115406A1-20200416-C00781
    Figure US20200115406A1-20200416-C00782
    Figure US20200115406A1-20200416-C00783
    Figure US20200115406A1-20200416-C00784
    Figure US20200115406A1-20200416-C00785
    Figure US20200115406A1-20200416-C00786
    Figure US20200115406A1-20200416-C00787
    Figure US20200115406A1-20200416-C00788
    Figure US20200115406A1-20200416-C00789
    Figure US20200115406A1-20200416-C00790
    Figure US20200115406A1-20200416-C00791
    Figure US20200115406A1-20200416-C00792
    Figure US20200115406A1-20200416-C00793
    Figure US20200115406A1-20200416-C00794
    Figure US20200115406A1-20200416-C00795
    Figure US20200115406A1-20200416-C00796
    Figure US20200115406A1-20200416-C00797
    Figure US20200115406A1-20200416-C00798
    Figure US20200115406A1-20200416-C00799
    Figure US20200115406A1-20200416-C00800
    Figure US20200115406A1-20200416-C00801
    Figure US20200115406A1-20200416-C00802
    Figure US20200115406A1-20200416-C00803
    Figure US20200115406A1-20200416-C00804
    Figure US20200115406A1-20200416-C00805
    Figure US20200115406A1-20200416-C00806
    Figure US20200115406A1-20200416-C00807
    Figure US20200115406A1-20200416-C00808
    Figure US20200115406A1-20200416-C00809
    Figure US20200115406A1-20200416-C00810
    Figure US20200115406A1-20200416-C00811
    Figure US20200115406A1-20200416-C00812
    Figure US20200115406A1-20200416-C00813
    Figure US20200115406A1-20200416-C00814
    Figure US20200115406A1-20200416-C00815
    Figure US20200115406A1-20200416-C00816
    Figure US20200115406A1-20200416-C00817
    Figure US20200115406A1-20200416-C00818
    Figure US20200115406A1-20200416-C00819
    Figure US20200115406A1-20200416-C00820
    Figure US20200115406A1-20200416-C00821
    Figure US20200115406A1-20200416-C00822
    Figure US20200115406A1-20200416-C00823
    Figure US20200115406A1-20200416-C00824
    Figure US20200115406A1-20200416-C00825
    Figure US20200115406A1-20200416-C00826
    Figure US20200115406A1-20200416-C00827
    Figure US20200115406A1-20200416-C00828
    Figure US20200115406A1-20200416-C00829
    Figure US20200115406A1-20200416-C00830
    Figure US20200115406A1-20200416-C00831
    Figure US20200115406A1-20200416-C00832
    Figure US20200115406A1-20200416-C00833
    Figure US20200115406A1-20200416-C00834
    Figure US20200115406A1-20200416-C00835
    Figure US20200115406A1-20200416-C00836
    Figure US20200115406A1-20200416-C00837
    Figure US20200115406A1-20200416-C00838
    Figure US20200115406A1-20200416-C00839
    Figure US20200115406A1-20200416-C00840
    Figure US20200115406A1-20200416-C00841
    Figure US20200115406A1-20200416-C00842
    Figure US20200115406A1-20200416-C00843
    Figure US20200115406A1-20200416-C00844
    Figure US20200115406A1-20200416-C00845
    Figure US20200115406A1-20200416-C00846
    Figure US20200115406A1-20200416-C00847
    Figure US20200115406A1-20200416-C00848
    Figure US20200115406A1-20200416-C00849
  • Figure US20200115406A1-20200416-C00850
    Figure US20200115406A1-20200416-C00851
    Figure US20200115406A1-20200416-C00852
    Figure US20200115406A1-20200416-C00853
    Figure US20200115406A1-20200416-C00854
    Figure US20200115406A1-20200416-C00855
    Figure US20200115406A1-20200416-C00856
    Figure US20200115406A1-20200416-C00857
    Figure US20200115406A1-20200416-C00858
    Figure US20200115406A1-20200416-C00859
    Figure US20200115406A1-20200416-C00860
    Figure US20200115406A1-20200416-C00861
    Figure US20200115406A1-20200416-C00862
    Figure US20200115406A1-20200416-C00863
    Figure US20200115406A1-20200416-C00864
    Figure US20200115406A1-20200416-C00865
    Figure US20200115406A1-20200416-C00866
    Figure US20200115406A1-20200416-C00867
    Figure US20200115406A1-20200416-C00868
    Figure US20200115406A1-20200416-C00869
    Figure US20200115406A1-20200416-C00870
    Figure US20200115406A1-20200416-C00871
    Figure US20200115406A1-20200416-C00872
    Figure US20200115406A1-20200416-C00873
    Figure US20200115406A1-20200416-C00874
  • Figure US20200115406A1-20200416-C00875
    Figure US20200115406A1-20200416-C00876
    Figure US20200115406A1-20200416-C00877
    Figure US20200115406A1-20200416-C00878
    Figure US20200115406A1-20200416-C00879
    Figure US20200115406A1-20200416-C00880
    Figure US20200115406A1-20200416-C00881
    Figure US20200115406A1-20200416-C00882
    Figure US20200115406A1-20200416-C00883
    Figure US20200115406A1-20200416-C00884
    Figure US20200115406A1-20200416-C00885
    Figure US20200115406A1-20200416-C00886
    Figure US20200115406A1-20200416-C00887
    Figure US20200115406A1-20200416-C00888
    Figure US20200115406A1-20200416-C00889
    Figure US20200115406A1-20200416-C00890
    Figure US20200115406A1-20200416-C00891
    Figure US20200115406A1-20200416-C00892
    Figure US20200115406A1-20200416-C00893
    Figure US20200115406A1-20200416-C00894
    Figure US20200115406A1-20200416-C00895
    Figure US20200115406A1-20200416-C00896
    Figure US20200115406A1-20200416-C00897
    Figure US20200115406A1-20200416-C00898
    Figure US20200115406A1-20200416-C00899
    Figure US20200115406A1-20200416-C00900
    Figure US20200115406A1-20200416-C00901
    Figure US20200115406A1-20200416-C00902
    Figure US20200115406A1-20200416-C00903
    Figure US20200115406A1-20200416-C00904
    Figure US20200115406A1-20200416-C00905
    Figure US20200115406A1-20200416-C00906
    Figure US20200115406A1-20200416-C00907
    Figure US20200115406A1-20200416-C00908
    Figure US20200115406A1-20200416-C00909
    Figure US20200115406A1-20200416-C00910
    Figure US20200115406A1-20200416-C00911
    Figure US20200115406A1-20200416-C00912
    Figure US20200115406A1-20200416-C00913
    Figure US20200115406A1-20200416-C00914
    Figure US20200115406A1-20200416-C00915
    Figure US20200115406A1-20200416-C00916
    Figure US20200115406A1-20200416-C00917
    Figure US20200115406A1-20200416-C00918
    Figure US20200115406A1-20200416-C00919
    Figure US20200115406A1-20200416-C00920
    Figure US20200115406A1-20200416-C00921
    Figure US20200115406A1-20200416-C00922
    Figure US20200115406A1-20200416-C00923
    Figure US20200115406A1-20200416-C00924
    Figure US20200115406A1-20200416-C00925
    Figure US20200115406A1-20200416-C00926
    Figure US20200115406A1-20200416-C00927
    Figure US20200115406A1-20200416-C00928
    Figure US20200115406A1-20200416-C00929
    Figure US20200115406A1-20200416-C00930
    Figure US20200115406A1-20200416-C00931
    Figure US20200115406A1-20200416-C00932
    Figure US20200115406A1-20200416-C00933
    Figure US20200115406A1-20200416-C00934
    Figure US20200115406A1-20200416-C00935
    Figure US20200115406A1-20200416-C00936
    Figure US20200115406A1-20200416-C00937
    Figure US20200115406A1-20200416-C00938
    Figure US20200115406A1-20200416-C00939
    Figure US20200115406A1-20200416-C00940
    Figure US20200115406A1-20200416-C00941
    Figure US20200115406A1-20200416-C00942
    Figure US20200115406A1-20200416-C00943
    Figure US20200115406A1-20200416-C00944
    Figure US20200115406A1-20200416-C00945
    Figure US20200115406A1-20200416-C00946
    Figure US20200115406A1-20200416-C00947
    Figure US20200115406A1-20200416-C00948
    Figure US20200115406A1-20200416-C00949
    Figure US20200115406A1-20200416-C00950
  • In Formula 1, A51 may be a C4-C60 alkyl group, A52 may be deuterium or a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, a51 (the number of A51) and a52 (the number of A52) may each independently be an integer from 0 to 10, provided that the sum of a51 and a52 may be 1 or more. That is, in Formula 1, ring CY51 is substituted with a group represented by A51, a group represented by A52, or any combination thereof. Since ring CY51 is substituted with an electron donating group, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan.
  • In an embodiment, A51 in Formula 1 may be a group having the formula —C(R511)(R512)(R513), wherein R511, R512, and R513 are each independently a C1-C60 alkyl group, for example, a C1-C50 alkyl group, a C1-C40 alkyl group, a C1-C30 alkyl group, a C1-C20 alkyl group, a C1-C10 alkyl group, or a C1-C5 alkyl group. While not wishing to be bound by theory, it is understood that when A51 has the formula —C(R511)(R512)(R513), the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan compared to the compounds in which at least one of R511, R512, or R513 is hydrogen.
  • In an embodiment, A52 in Formula 1 may be a group having the formula —CD(R521)(R522), wherein R521 and R522 are each independently a C1-C60 alkyl group, a C1-C60 alkyl group substituted with deuterium, a C3-C10 cycloalkyl group, or any combination thereof. In an embodiment, A52 in Formula 1 may be a group having the formula —CD2(R521), wherein R521 is the same as defined above. In still another embodiment, A52 may be a fully deuterated group, such as CD3, C2D5, C3D7, C4D9, but is not limited thereto. While not wishing to be bound by theory, it is understood that when A52 has the formula —CD(R521)(R522), the formula —CD2(R521), or wherein A52 is a fully deuterated group, the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan compared to the compounds in which at least one of R521 or R522 is hydrogen.
  • A52 may be a partially or fully deuterated C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group. When the degree of deuteration is 100%, the group A52 is fully deuterated. When the degree of deuteration is lower than 100%, the group A52 is partially deuterated. The degree of deuteration of the group A52 may be calculated by using Equation 10:

  • degree of deuteration (%)=n D2/(n H2 +n D2)×100.  Equation 10
  • In Equation 10, nH2 represents the total number of hydrogens included in the group A52, and
  • nD2 represents the total number of deuterium atoms included in the group A52.
  • In an embodiment, the degree of deuteration of the group A52 may be about 5% or more, about 10% or more, about 20% or more, about 30% or more, about 40% or more, about 50% or more, about 60% or more, about 70% or more, about 90% or more, about 95% or more, about 96% or more, about 97% or more, about 98% or more, or about 99% or more, but embodiments of the present disclosure are not limited thereto.
  • In addition, a53 that is the number of groups represented by
  • Figure US20200115406A1-20200416-C00951
  • in Formula 1 may be an integer from 1 to 10. That is, since a53 in Formula 1 is not 0, ring CY51 in Formula 1 is substituted with a group represented by
  • Figure US20200115406A1-20200416-C00952
  • Therefore, due to the resonance effect caused by the group represented by
  • Figure US20200115406A1-20200416-C00953
  • an electronic device, for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan. In addition, although not limited by a specific theory, a group represented by
  • Figure US20200115406A1-20200416-C00954
  • in Formula 1 is protected from electrons, heat, or the like by the group represented by
  • Figure US20200115406A1-20200416-C00955
  • Therefore, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1, may have improved luminescent efficiency and lifespan.
  • In Formula 1, the sum of a51 and a52 may be 1 or more and a53 may be an integer from 1 to 10. Thus, in an embodiment, the organometallic compound may simultaneously include
  • Figure US20200115406A1-20200416-C00956
  • and A51. In another embodiment, the organometallic compound may simultaneously include
  • Figure US20200115406A1-20200416-C00957
    • and A52.
  • For example, highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), energy band gap, singlet (Si), and triplet (Ti) energy levels of Compounds 1 to 8 were evaluated by using a DFT method of Gaussian program (structurally optimized at a level of B3LYP, 6-31G(d,p)). Evaluation results are shown in Table 1 below.
  • TABLE 1
    Energy
    Compound HOMO LUMO band gap S1 T1
    No. (eV) (eV) (eV) (eV) (eV)
    1 −4.647 −1.681 2.965 2.489 2.333
    2 −4.660 −1.694 2.966 2.489 2.334
    3 −4.584 −1.642 2.942 2.486 2.336
    4 −4.584 −1.642 2.942 2.486 2.336
    5 −4.647 −1.681 2.965 2.489 2.333
    6 −4.647 −1.681 2.965 2.489 2.333
    7 −4.598 −1.624 2.974 2.488 2.344
    8 −4.621 −1.695 2.926 2.486 2.311
  • Figure US20200115406A1-20200416-C00958
    Figure US20200115406A1-20200416-C00959
    Figure US20200115406A1-20200416-C00960
  • From Table 1, it is confirmed that the organometallic compound represented by Formula 1 has such electric characteristics that are suitable for use in an electronic device, for example, for use as a dopant for an organic light-emitting device.
  • Synthesis methods of the organometallic compound represented by Formula 1 may be understood by one of ordinary skill in the art by referring to Synthesis Examples provided below.
  • The organometallic compound represented by Formula 1 is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Thus, another aspect provides an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer and an organometallic compound represented by Formula 1.
  • The organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1, a low driving voltage, high quantum efficiency, a low roll-off ratio, and a long lifespan.
  • The organometallic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this embodiment, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1 is smaller than an amount of the host).
  • In an embodiment, the emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1. The organometallic compound represented by Formula 1 may be a red phosphorescent dopant.
  • The expression “(an organic layer) includes an organometallic compound” as used herein may include an embodiment in which “(an organic layer) includes identical organometallic compounds represented by Formula 1” and an embodiment in which “(an organic layer) includes two or more different organometallic compounds represented by Formula 1.”
  • For example, the organic layer may include, as the organometallic compound, only Compound 1. In this embodiment, Compound 1 may be included in an emission layer of the organic light-emitting device. In an embodiment, the organic layer may include, as the organometallic compound, Compound 1 and Compound 2. In this embodiment, Compound 1 and Compound 2 may be included in an identical layer (for example, Compound 1 and Compound 2 may both be included in an emission layer).
  • The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.
  • In an embodiment, in the organic light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
  • The FIGURE is a schematic view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with the FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
  • A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.
  • The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material(s) with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). In an embodiment, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-L1), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the first electrode.
  • The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
  • The organic layer 15 is disposed on the first electrode 11.
  • The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
  • The hole transport region may be disposed between the first electrode 11 and the emission layer.
  • The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
  • The hole transport region may include only either a hole injection layer or a hole transport layer. In an embodiment, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.
  • A hole injection layer may be formed on the first electrode 11 by using a suitable method for example, vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, or any combination thereof.
  • When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a compound that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10−8 torr to about 10−3 torr, and a deposition rate of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.
  • When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
  • Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
  • The hole transport region may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzene sulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrene sulfonate) (PANI/PSS), a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
  • Figure US20200115406A1-20200416-C00961
    Figure US20200115406A1-20200416-C00962
    Figure US20200115406A1-20200416-C00963
  • In Formula 201, Ar101 and Ar102 may each independently be a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.
  • In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may be 0, 1, or 2. For example, xa is 1 and xb is 0, but xa and xb are not limited thereto.
  • In Formulae 201 and 202, R101 to R108, R111 to R119, and R121 to R124 may each independently be:
  • a hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and so on), or a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and so on);
  • a C1-C10 alkyl group or a C1-C10 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or any combination thereof; or
  • a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, a C1-C10 alkoxy group or any combination thereof,
  • but embodiments of the present disclosure are not limited thereto.
  • In Formula 201, R109 may be a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof.
  • In an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments of the present disclosure are not limited thereto:
  • Figure US20200115406A1-20200416-C00964
  • In Formula 201A, R101, R111, R112, and R109 are each independently the same as described above.
  • For example, the compound represented by Formula 201 and the compound represented by Formula 202 may each independently include Compounds HT1 to HT20, but are not limited thereto:
  • Figure US20200115406A1-20200416-C00965
    Figure US20200115406A1-20200416-C00966
    Figure US20200115406A1-20200416-C00967
    Figure US20200115406A1-20200416-C00968
    Figure US20200115406A1-20200416-C00969
    Figure US20200115406A1-20200416-C00970
  • A thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, and for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, and for example, about 100 Å to about 1,500 Å. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
  • The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
  • The charge-generation material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a cyano group-containing compound, such as Compound HT-D1, but are not limited thereto.
  • Figure US20200115406A1-20200416-C00971
  • The hole transport region may include a buffer layer.
  • Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
  • Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be a material(s) for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.
  • Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a compound that is used to form the emission layer.
  • The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1.
  • The host may include TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, or any combination thereof:
  • Figure US20200115406A1-20200416-C00972
    Figure US20200115406A1-20200416-C00973
  • When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer. In an embodiment, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
  • When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
  • The dopant may include the organometallic compound represented by Formula 1. For example, the dopant may be a red phosphorescent dopant.
  • A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
  • Then, an electron transport region may be disposed on the emission layer.
  • The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
  • For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.
  • Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
  • When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAIq, or any combination thereof, but embodiments of the present disclosure are not limited thereto:
  • Figure US20200115406A1-20200416-C00974
  • A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking ability without a substantial increase in driving voltage.
  • The electron transport layer may include BCP, Bphen, Alq3, BAIq, TAZ, NTAZ, or any combination thereof:
  • Figure US20200115406A1-20200416-C00975
  • In an embodiment, the electron transport layer may include at least one of ET1 to ET25, but are not limited thereto:
  • Figure US20200115406A1-20200416-C00976
    Figure US20200115406A1-20200416-C00977
    Figure US20200115406A1-20200416-C00978
    Figure US20200115406A1-20200416-C00979
    Figure US20200115406A1-20200416-C00980
    Figure US20200115406A1-20200416-C00981
    Figure US20200115406A1-20200416-C00982
    Figure US20200115406A1-20200416-C00983
  • A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
  • Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
  • The metal-containing material may include a L1 complex. The L1 complex may include, for example, Compound ET-D1 (lithium 8-hydroxyquinolate, LiQ) or ET-D2:
  • Figure US20200115406A1-20200416-C00984
  • The electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.
  • The electron injection layer may include LiF, NaCl, CsF, L12O, BaO, or any combination thereof.
  • A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
  • The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, or any combination thereof, which have a relatively low work function. For example, lithium (L1), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-L1), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as a material for forming the second electrode 19. In an embodiment, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
  • Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments of the present disclosure are not limited thereto.
  • Another aspect of the present disclosure provides a diagnostic composition including an organometallic compound represented by Formula 1.
  • The organometallic compound represented by Formula 1 provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
  • The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.
  • The term “C1-C60 alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. The term “C1-C60 alkylene group” as used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
  • The term “C1-C60 alkoxy group” as used herein refers to a monovalent group represented by —OA101(wherein A101 is the C1-C60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy group.
  • The term “C2-C60 alkenyl group” as used herein refers to a hydrocarbon group formed by including a carbon-carbon double bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C2-C60 alkenylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
  • The term “C2-C60 alkynyl group” as used herein refers to a hydrocarbon group formed by including a carbon-carbon triple bond in the middle or at the terminus of the C2-C60 alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C2-C60 alkynylene group” as used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
  • The term “C3-C10 cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C3-C10 cycloalkylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
  • The term “C2-C10 heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group having an N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom and 1 to 10 carbon atoms, and non-limiting examples thereof include a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C2-C10 heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C2-C10 heterocycloalkyl group.
  • The term “C3-C10 cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and a carbon-carbon double bond in the ring thereof and that has no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C3-C10 cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
  • The term “C2-C10 heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has an N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom, 1 to 10 carbon atoms, and a carbon-carbon double bond in its ring. Examples of the C2-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C1-C10 heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C2-C10 heterocycloalkenyl group.
  • The term “C6-C60 aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C6-C60 arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
  • The term “C7-C60 alkylaryl group” as used herein refers to a C1-C60 aryl group substituted with a C1-C54 alkyl group.
  • The term “C1-C60 heteroaryl group” as used herein refers to a monovalent group having an aromatic system that has an N, O, P, Si, Se, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. The term “C1-C60 heteroarylene group” as used herein refers to a divalent group having an aromatic system that has an N, O, P, Se, S, or any combination thereof as a ring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples of the C1-C60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C1-C60 heteroaryl group and the C1-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
  • The term “C2-C60 alkylheteroaryl group” as used herein refers to a C1-C60 heteroaryl group substituted with a C1-C60 alkyl group.
  • The term “C6-C60 aryloxy group” as used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), a C6-C60 arylthio group as used herein indicates —SA103 (wherein A103 is the C6-C60 aryl group), and the term “C7-C60 arylalkyl group” as used herein indicates —A104A105 (wherein A105 is the C6-C59 aryl group and A104 is the C1-C54 alkylene group).
  • The term “C1-C60 heteroaryloxy group” as used herein refers to —OA106 (wherein A106 is the C2-C60 heteroaryl group), the term “C1-C60 heteroarylthio group” as used herein indicates —SA107 (wherein A107 is the C1-C60 heteroaryl group), and the term “C2-C60 heteroarylalkyl group” as used herein refers to —A108A109 (A109 is a C1-C59 heteroaryl group, and A108 is a C1-C59 alkylene group).
  • The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed to each other, only carbon atoms as ring-forming atoms, and having no aromaticity in its entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
  • The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, an N, O, P, Si, Se, S, or any combination thereof and carbon atoms, as ring-forming atoms, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
  • The term “C5-C30 carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C5-C30 carbocyclic group may be a monocyclic group or a polycyclic group.
  • The term “C2-C30 heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, an N, O, Si, P, Se, S, or any combination thereof and 1 to 30 carbon atoms. The C2-C30 heterocyclic group may be a monocyclic group or a polycyclic group.
  • A substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C2-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:
  • a deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
  • a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
  • a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
  • —N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
  • any combination thereof. For example, a CH2CN group is a C1 group substituted with a nitrile.
  • Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 in this disclosure may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C2-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C7-C60 arylalkyl group; a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group; a C1-C60 heteroarylthio group; a C2-C60 heteroarylalkyl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
  • Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The expression “‘A’ is used instead of ‘B’” used in describing Synthesis Examples means that a molar equivalent of “A” was identical to a molar equivalent of “B”.
    • EXAMPLES Synthesis Example 1 (Compound 6)
  • Figure US20200115406A1-20200416-C00985
  • Synthesis of Intermediate 6-3
  • 2.4 grams (g) (0.006 millimoles (mmol), 1.2 equivalents, equiv.) of Intermediate 2-2, 1.4 g (0.005 mmol, 1 equiv.) of Intermediate 1-1, 0.40 g (0.001 mmol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 2.0 g (0.015 mmol, 3 equiv.) of potassium carbonate were dissolved in 20 milliliters (mL) of a solvent in which tetrahydrofuran (THF) and distilled water (H2O) were mixed at a ratio of 3:1, and the reaction mixture was refluxed for 12 hours. The reaction mixture obtained therefrom was cooled to room temperature, and the precipitate was filtered to obtain a filtrate. The filtrate was washed by using ethyl acetate (EA)/H2O and the crude product was purified by column chromatography (gradient elution of EA/hexane (Hex) from 20% to 35%) to obtain 2.2 g (yield of 68%) of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C58H53D8N3O m/z 823.5317, Found: 823.5319.
  • Synthesis of Compound 6
  • 2.2 g (2.26 mmol) of Intermediate 6-3 and 1.1 g (2.26 mmol, 1.0 equiv.) of K2PtCl4 were dissolved in 40 mL of a solvent in which 30 mL of AcOH and 10 mL of H2O were mixed, and the reaction mixture was refluxed for 16 hours. The reaction mixture obtained therefrom was cooled to room temperature, and the precipitate was filtered. The precipitate was dissolved again in MC and washed by using H2O. The crude product was purified by column chromatography (methylene chloride (MC) 40%, EA 1%, Hex 59%) to obtain 1.6 g (yield of 60%) of Compound 6. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C58H51D8N3OPt: m/z 1016.4808, Found: 1016.4805.
    • Synthesis Example 2 (Compound 1)
  • Figure US20200115406A1-20200416-C00986
  • Synthesis of Intermediate 1-3
  • Intermediate 1-3 1.2 g (yield of 65%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 1-2 was used instead of Intermediate 2-2. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C59H56D7N3O: m/z 836.5411, Found: 836.5414.
  • Synthesis of Compound 1
  • Compound 1 1.0 g (yield of 68%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 1-3 was used instead of Intermediate 6-3. The obtained compound was identified by mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C59H54D7N3OPt: m/z 1029.4902, Found: 1029.4901.
    • Synthesis Example 3 (Compound 2)
  • Figure US20200115406A1-20200416-C00987
  • Synthesis of Intermediate 2-3
  • Intermediate 2-3 2.1 g (yield of 70%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 2-1 was used instead of Intermediate 1-1. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C58H53D8N3O: m/z 823.5317, Found: 823.5319.
  • Synthesis of Compound 2
  • Compound 2 1.84 g (yield of 71%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 2-3 was used instead of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C58H51D8N3OPt: m/z 1016.4808, Found: 1016.4809.
    • Synthesis Example 4 (Compound 3)
  • Figure US20200115406A1-20200416-C00988
  • Synthesis of Intermediate 3-3
  • Intermediate 3-3 1.7 g (yield of 72%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 3-2 was used instead of Intermediate 2-2. The obtained compound was identified by Mass and HPLC analysis.
  • HRMS (MALDI) calcd for C59H63N3O: m/z 829.4971, Found: 829.4973.
  • Synthesis of Compound 3
  • Compound 3 1.53 g (yield of 73%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 3-3 was used instead of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C59H61N3OPt: m/z 1022.4462, Found: 1022.4461.
    • Synthesis Example 5 (Compound 4)
  • Figure US20200115406A1-20200416-C00989
  • Synthesis of Intermediate 4-3
  • Intermediate 4-3 1.85 g (yield of 73%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 4-2 was used instead of Intermediate 2-2. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C59H60D3N3O: m/z 832.5159, Found 832.52.
  • Synthesis of Compound 4
  • Compound 4 1.64 g (yield of 72%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 4-3 was used instead of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C59H58D3N3OPt: m/z 1025.4651, Found: 1025.4652.
    • Synthesis Example 6 (Compound 5)
  • Figure US20200115406A1-20200416-C00990
  • Synthesis of Intermediate 5-3
  • Intermediate 5-3 2 g (yield of 68%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 5-1 and Intermediate 5-2 were used instead of Intermediate 1-1 and Intermediate 2-2. The obtained compound was identified by Mass and HPLC analysis.
  • HRMS (MALDI) calcd for C58H61N3O: m/z 815.4815, Found: 815.4813.
  • Synthesis of Compound 5
  • Compound 5 1.73 g (yield of 70%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 5-3 was used instead of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C58H59N3OPt: m/z 1008.4306, Found: 1008.4308.
    • Synthesis Example 7 (Compound 7)
  • Figure US20200115406A1-20200416-C00991
  • Synthesis of Intermediate 7-3
  • Intermediate 7-3 1.8 g (yield of 69%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 7-2 was used instead of Intermediate 2-2. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C60H59D6N3O: m/z 849.5504, Found: 849.5502.
  • Synthesis of Compound 7
  • Compound 7 1.65 g (yield of 75%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 7-3 was used instead of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C60H57D6N3OPt: m/z 1042.4995, Found: 1042.4996.
    • Synthesis Example 8 (Compound 8)
  • Figure US20200115406A1-20200416-C00992
  • Synthesis of Intermediate 8-3
  • Intermediate 8-3 1.7 g (yield of 65%) was obtained in the same manner as in the synthesis of Intermediate 6-3 of Synthesis Example 1, except that Intermediate 8-2 was used instead of Intermediate 2-2. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C64H65N3O m/z 891.5128, Found: 891.5127.
  • Synthesis of Compound 8
  • Compound 8 1.41 g (yield of 68%) was obtained in the same manner as in the synthesis of Compound 6 of Synthesis Example 1, except that Intermediate 8-3 was used instead of Intermediate 6-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C64H63N3OPt m/z 1084.4619, Found: 1084.4617.
    • Synthesis Example 9 (Compound 9)
  • Figure US20200115406A1-20200416-C00993
  • Synthesis of Intermediate 9-3
  • Intermediate 9-3 2.1 g (yield of 63%) was obtained in the same manner as in the synthesis of Intermediate 4-3 of Synthesis Example 5, except that Intermediate 9-1 was used instead of Intermediate 1-1. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C61H60D5N3O m/z 860.5441 Found 860.5443.
  • Synthesis of Compound 9
  • Compound 9 1.77 g (yield of 69%) was obtained in the same manner as in the synthesis of Compound 4 of Synthesis Example 5, except that Intermediate 9-3 was used instead of Intermediate 4-3. The obtained compound was identified by Mass spectrum and HPLC analysis.
  • HRMS (MALDI) calcd for C61H58D5N3OPt m/z 1053.4933 Found 1053.4932.
    • Evaluation Example 1 Evaluation of Photoluminescence Quantum Yield (PLQY) and Radiative Decay Rate
  • CBP and Compound 1 were co-deposited at a weight ratio of 9:1 at a vacuum pressure of 10−7 torr to manufacture a film having a thickness of 40 nanometers (nm).
  • A PLQY of the film was evaluated by using a Hamamatsu Photonics absolute PL quantum yield measurement system including a xenon light source, a monochromator, a photonic multichannel analyzer, an integrating sphere and employing a PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan), and a PLQY of Compound 1 was confirmed. The results of this study are shown in Table 2.
  • A PL spectrum of the film was evaluated at room temperature by using a PicoQuant TRPL measurement system FluoTime 300 and a PicoQuant pumping source PLS340 (excitation wavelength=340 nm, spectral width=20 nm), a wavelength of a main peak of the spectrum was determined, PLS340 repeatedly measured the number of photons emitted from the film at the wavelength of the main peak due to a photon pulse (pulse width=500 picoseconds, ps) applied to the film according to time based on time-correlated single photon counting (TCSPC), thereby obtaining a sufficiently fittable TRPL curve. Tdecay(Ex) (decay time) of the film was obtained by fitting one or more exponential decay functions to the result obtained therefrom, and the radiative decay rate that is a reciprocal of Tdecay(Ex) was calculated. The results are shown in Table 2. The function used for fitting is expressed by Equation 20, and the greatest value of Tdecay obtained from each exponential decay function used for fitting was taken as Tdecay(Ex). At this time, a baseline or background signal curve was obtained by repeating the same measurement once more for the same measurement time as the measurement time for obtaining the TRPL curve in a dark state (a state in which a pumping signal applied to the predetermined film was blocked), and the baseline or background signal curve was used for fitting as a baseline.
  • f ( t ) = ∑ i = 1 n A i exp ( - t / T decay , i ) Equation 20
  • The measurement of the PLQY and the radiative decay time was performed on Compounds 2 to 9, and results thereof are shown in Table 2.
  • TABLE 2
    Compound Radiative decay rate
    No. PLQY (%) (s−1)
    1 0.999 4.15 × 105
    2 0.992 4.09 × 105
    3 0.999 4.81 × 105
    4 0.999 4.85 × 105
    5 0.999 4.99 × 105
    6 0.999 4.93 × 105
    7 0.998 4.90 × 105
    8 0.999 4.83 × 105
    9 0.999 4.16 × 105
    *s−1 = reverse seconds
  • Figure US20200115406A1-20200416-C00994
    Figure US20200115406A1-20200416-C00995
    Figure US20200115406A1-20200416-C00996
  • Referring to Table 2, it is confirmed that Compounds 1 to 9 have a high PLQY and a high radiative decay rate.
    • Evaluation Example 2: Evaluation of Horizontal Orientation Ratio
  • mCP and Compound 1 were co-deposited on a fused silica base layer (thickness of 1 mm) at a weight ratio of 92:8 in a vacuum deposition apparatus having a vacuum pressure of 1×10−7 torr to form Sample 1 having a thickness of 30 nm (8 weight %), and Sample 1 was sealed with glass and glue in a nitrogen atmosphere. This procedure was repeated on Compounds shown in Table 3 to manufacture Samples 2 to 9.
  • Meanwhile, an angle-dependent PL measurement apparatus having a structure illustrated in FIG. 3 of Korean Patent Application No. 10-2013-0150834, the content of which is incorporated herein in its entirety by reference, was prepared. Detailed specifications are as follows:
      • Excited light wavelength: 325 nm
      • Excited light supply source: He—Cd laser, Melles Griot
      • Excited light irradiation means: Optical fiber, diameter of 1 millimeter (mm), Thorlabs
      • Semi-cylindrical prism: Fused silica, diameter of 100 mm, length of 30 mm
      • Emitted light detection means: Photomultiplier tube, Acton
      • Polarizer mounted on emitted light detection means: Linear polarizer, Thorlabs
      • Recording apparatus: SpectraSense, Acton
      • Excited light incidence angle: θP=45°, θH=0°
      • Distance from sample to emitted light detection means (or radius of moving path of emitted light detection means): 900 mm
  • Then, each of Samples 1 to 8 was fixed on a semi-cylindrical lens, and a 325-nm laser was irradiated to emit light. The emitted light passed through a polarization film, and p-polarization light emission strength was measured with respect to 530-nm light of 90° to 0° while turning by 1° with respect to the axis of the semi-cylindrical lens, to which the sample was fixed, by using a charge-coupled device (CCD).
  • p-Polarization light emission strength (first p-polarization light emission strength) appearing when each Compound has a vertical orientation and p-polarization light emission strength (second p-polarization light emission strength) appearing when each Compound had a horizontal orientation were calculated with respect to 0° to 90°. The weights at which p-polarization light emission strength were calculated by multiplying each weight by the first and second p-polarization light emission strengths coinciding with the measured p-polarization light emission strength, and the horizontal orientation ratios of Compounds shown in Table 3 were measured. The results of this study are shown in Table 3. The angle-dependent PL spectrum was analyzed by using a classical dipole moment regarded as dissipated power from a dipole oscillating light emission from excitons.
  • TABLE 3
    Horizontal orientation
    Sample No. Co-deposition material ratio (%)
    1 mCP Compound 1 (8 weight %) 90%
    2 mCP Compound 2 (8 weight %) 90%
    3 mCP Compound 3 (8 weight %) 88%
    4 mCP Compound 4 (8 weight %) 88%
    5 mCP Compound 5 (8 weight %) 90%
    6 mCP Compound 6 (8 weight %) 90%
    7 mCP Compound 7 (8 weight %) 90%
    8 mCP Compound 8 (8 weight %) 90%
    9 mCP Compound 9 (8 weight %) 90%
    * weight % = percent by weight
  • Referring to Table 3, it is confirmed that Compound 1 to 9 have excellent horizontal orientation ratios, that is, excellent horizontal optical orientation.
    • Example 1
  • As an anode, a glass substrate, on which ITO/Ag/ITO (70 Å/1,000 Å/70 Å) were deposited, was cut to a size of 50 mm×50 mm×0.5 mm, sonicated with iso-propyl alcohol and pure water each for 5 minutes, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate was provided to a vacuum deposition apparatus.
  • 2-TNATA was vacuum-deposited on the anode of the glass substrate to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 1,350 Å.
  • CBP (host) and Compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 94:6 to form an emission layer having a thickness of 400 Å.
  • Then, BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, Alq3 was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and MgAg was deposited on the electron injection layer at a weight ratio of 90:10 to form a cathode having a thickness of 120 Å, thereby completing an organic light-emitting device having a structure of anode/2-TNATA (600 Å)/NPB (1,350 Å)/CBP+Compound 1 (6 weight %) (400 Å)/BCP (50 Å)/Alq3 (350 Å) /LiF (10 Å)/MgAg (120 Å).
  • Figure US20200115406A1-20200416-C00997
    • Examples 2 to 9 and Comparative Examples a to E
  • Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compound shown in Table 4 were each used instead of Compound 1 as a dopant in forming an emission layer.
    • Evaluation Example 3: Evaluation of Characteristics of Organic Light-Emitting Devices
  • The driving voltage, current density, maximum quantum efficiency, roll-off ratio, full width at half maximum (FWHM), peak emission wavelength, and lifespan of the organic light-emitting devices manufactured according to Examples 1 to 9 and Comparative Example A to E were evaluated by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A), and results thereof are shown in Tables 4 and 5. The roll-off ratio was calculated by Equation 30. The lifespan (LT99, at 3,500 nit) indicates an amount of time that elapsed when luminance was 99% of initial luminance (100%) and is expressed by a relative value (%).

  • roll off ratio={1−(efficiency (at 3,500 nit)/maximum luminescent efficiency)}×100%  Equation 30
  • TABLE 4
    Maximum Roll-
    Dopant Driving Current quantum off
    compound voltage density efficiency ratio FWHM
    No. (V) (mA/cm2) (%) (%) (nm)
    Example 1 1 3.69 10 112 9 68
    Example 2 2 3.72 10 102 6 68
    Example 3 3 3.79 10 107 8 68
    Example 4 4 3.79 10 109 9 67
    Example 5 5 3.83 10 99 7 69
    Example 6 6 4.60 10 108 10 70
    Example 7 7 3.84 10 111 8 67
    Example 8 8 3.80 10 114 7 67
    Example 9 9 3.96 10 110 7 67
    Comparative A 3.94 10 94 10 68
    Example A
    Comparative B 4.08 10 93 8 68
    Example B
    Comparative C 3.85 10 98 4 68
    Example C
    Comparative D 3.90 10 88 8 67
    Example D
    Comparative E 4.39 10 88 17 64
    Example E
  • TABLE 5
    Dopant Peak emission Lifespan (LT99)
    compound wavelength (at 3,500 nit)
    No. (nm) a relative value (%)
    Example 1 1 521 115%
    Example 2 2 523 110%
    Example 3 3 521 113%
    Example 4 4 521 115%
    Example 5 5 526 110%
    Example 6 6 525 130%
    Example 7 7 524 110%
    Example 8 8 527 180%
    Example 9 9 523 105%
    Comparative Example A 523  29%
    A
    Comparative Example B 526  50%
    B
    Comparative Example C 523  60%
    C
    Comparative Example D 520   3%
    D
    Comparative Example E 502   1%
    E
  • Figure US20200115406A1-20200416-C00998
    Figure US20200115406A1-20200416-C00999
    Figure US20200115406A1-20200416-C01000
    Figure US20200115406A1-20200416-C01001
  • Referring to Tables 4 and 5, it is confirmed that the organic light-emitting devices of Examples 1 to 9 have improved driving voltage, improved maximum quantum efficiency, and/or improved roll-off ratio, and also have improved lifespan characteristics, as compared with those of the organic light-emitting devices of Comparative Examples A to E.
  • Since the organometallic compound may emit light having a relatively small FWHM and have excellent PLQY, excellent radiative decay rate, and excellent horizontal orientation ratio, the organic light-emitting device including the organometallic compound may have improved driving voltage, external quantum efficiency, roll-off ratio, and lifespan characteristics. In addition, since the organometallic compound has excellent phosphorescence characteristics, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.
  • It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.
  • While embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present description as defined by the following claims.

Claims (20)

What is claimed is:
1. An organometallic compound represented by Formula 1:
Figure US20200115406A1-20200416-C01002
wherein, in Formula 1,
M is a transition metal,
X1 is O or S, wherein a bond between X1 and M is a covalent bond,
X2 to X4 are each independently C or N,
a bond between X2 and M, a bond between X3 and M, or a bond between X4 and M is a covalent bond, and the other bonds of a bond between X2 and M, a bond between X3 and M, and a bond between X4 and M are coordinate bonds,
Y1 and Y3 to Y5 are each independently C or N,
a bond between X2 and Y3, a bond between X2 and Y4, and a bond between Y4 and Y5 is a chemical bond,
ring CY1 to ring CY4 and ring CY51 are each independently a C5-C30 carbocyclic group or a C2-C30 heterocyclic group,
a cyclometalated ring formed by ring CY5, ring CY2, ring CY3, and M is a 6-membered ring,
T1 is a single bond, a double bond, *—N(R5)—*′, *—B(R5)—*′, *—P(R5)—*′, *—C(R5)(R6)—*′, *—Si(R5)(R6)—*′, *—Ge(R5)(R6)—*′, *—S—*, *—Se—*′, * *, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)2—*, * C(R5)=*′, *═C(R5)—*′, *—C(R5)═C(R6)—*′, *—C(═S)—*′, or *—C≡C—*′, wherein * and *′ each indicate a binding site to a neighboring atom,
L1 to L4 and L51 are each independently a single bond, a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group, or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
b1 to b4 and b51 are each independently an integer from 1 to 5,
R1 to R6, R51, and R52 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C7-C60 arylalkyl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted C1-C60 heteroaryloxy group, a substituted or unsubstituted C1-C60 heteroarylthio group, a substituted or unsubstituted C2-C60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), —Ge(Q3)(Q4)(Q5), —B(Q6)(Q7), —P(═O)(Q8)(Q9), or —P(Q8)(Q9),
c1 to c4, c51 and c52 are each independently an integer from 1 to 5,
A51 is a C4-C60 alkyl group,
A52 is deuterium or a deuterium-containing C1-C60 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group,
a1 to a4, a51, and a52 are each independently an integer from 0 to 10, provided that the sum of a51 and a52 is 1 or more,
a53 is an integer from 1 to 10,
two or more groups of a plurality of R1 groups are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of a plurality of R2 groups are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of a plurality of R3 groups are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of a plurality of R4 groups are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of R1 to R6 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
R10a is the same as described in connection with R1,
a substituent of the substituted C1-C60 alkyl group, the substituted C2-C60 alkenyl group, the substituted C2-C60 alkynyl group, the substituted C1-C60 alkoxy group, the substituted C3-C10 cycloalkyl group, the substituted C2-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C2-C10 heterocycloalkenyl group, the substituted C6-C60 aryl group, the substituted C6-C60 aryloxy group, the substituted C6-C60 arylthio group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C7-C60 arylalkyl group, the substituted C1-C60 heteroaryl group, the substituted C1-C60 heteroaryloxy group, the substituted C1-C60 heteroarylthio group, the substituted C2-C60 heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, or a C1-C60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), —Ge(Q13)(Q14)(Q15), —B(Q16)(Q17), —P(═O)(Q18)(Q19), —P(Q18)(Q19), or any combination thereof;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C7-C60 arylalkyl group, a C1-C60 heteroaryl group, a C1-C60 heteroaryloxy group, a C1-C60 heteroarylthio group, a C2-C60 heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), —Ge(Q23)(Q24)(Q25), —B(Q26)(Q27), —P(═O)(Q28)(Q29), —P(Q28)(Q29), or any combination thereof;
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), —Ge(Q33)(Q34)(Q35), —B(Q36)(Q37), —P(═O)(Q38)(Q39), or —P(Q38)(Q39); or
any combination thereof; and
Q1 to Q9, Q11 to Q19, Q21 to Q29, and Q31 to Q39 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C1-C60 alkyl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C2-C60 alkenyl group; a C2-C60 alkynyl group; a C1-C60 alkoxy group; a C3-C10 cycloalkyl group; a C2-C10 heterocycloalkyl group; a C3-C10 cycloalkenyl group; a C2-C10 heterocycloalkenyl group; a C6-C60 aryl group unsubstituted or substituted with deuterium, a C1-C60 alkyl group, a C6-C60 aryl group, or any combination thereof; a C6-C60 aryloxy group; a C6-C60 arylthio group; a C7-C60 arylalkyl group; a C1-C60 heteroaryl group; a C1-C60 heteroaryloxy group; a C1-C60 heteroarylthio group; a C2-C60 heteroarylalkyl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.
2. The organometallic compound of claim 1, wherein
M is Pt, Pd, or Au.
3. The organometallic compound of claim 1, wherein
A51 is an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-iso-pentyl group, unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentyl group, or any combination thereof, and
A52 is a deuterium-containing linear or branched C1-C20 alkyl group unsubstituted or substituted with a C3-C10 cycloalkyl group, in which the linear or branched C1-C20 alkyl group is a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, or a sec-iso-pentyl group, each unsubstituted or substituted with a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-iso-pentyl group, or any combination thereof.
4. The organometallic compound of claim 1, wherein
a3 and a4 are not 0, and
a group represented by *-(L3)b3-(R3)c3, and a group represented by *-(L4)b4-(R4)c4 are not hydrogen.
5. The organometallic compound of claim 1, wherein
a3 is not 0, and
an *-(L3)b3-(R3)c3 in a number of a3 satisfies Condition A and Condition B:
Condition A
L3 is a single bond,
Condition B
R3 is
hydrogen, deuterium, —F, a cyano group, C1-C20 alkyl group, or a C1-C20 alkoxy group;
a C1-C20 alkyl group or a C1-C20 alkoxy group, each substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof; or
a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
6. The organometallic compound of claim 1, wherein
a4 is not 0, and
a group represented by *-(L4)b4-(R4)c4 in a number of a4 satisfies Condition 1, Condition 2, or combination thereof:
Condition 1
An R4 in a number of c4 is a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C1-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,
Condition 2
L4 is not a single bond.
7. The organometallic compound of claim 1, wherein
a4 is not 0, and
an *-(L4)b4-(R4)c4 in a number of a4 satisfies Condition 1(1), Condition 2(1), or combination thereof:
Condition 1(1)
An R4 in a number of c4 is a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, or a terphenyl group, each unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof,
Condition 2(1)
L4 is a benzene group unsubstituted or substituted with deuterium, —F, —CD3, —CD2H, —CDH2, —CF3, —CF2H, —CFH2, a cyano group, a C1-C20 alkyl group, a deuterium-containing C2-C20 alkyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a (C1-C20 alkyl)cyclopentyl group, a (C1-C20 alkyl)cyclohexyl group, a (C1-C20 alkyl)cycloheptyl group, a (C1-C20 alkyl)cyclooctyl group, a (C1-C20 alkyl)adamantyl group, a (C1-C20 alkyl)norbornenyl group, a (C1-C20 alkyl)cyclopentenyl group, a (C1-C20 alkyl)cyclohexenyl group, a (C1-C20 alkyl)cycloheptenyl group, a (C1-C20 alkyl)bicyclo[1.1.1]pentyl group, a (C1-C20 alkyl)bicyclo[2.1.1]hexyl group, a (C1-C20 alkyl)bicyclo[2.2.1]heptyl group, a (C1-C20 alkyl)bicyclo[2.2.2]octyl group, a phenyl group, a (C1-C20 alkyl)phenyl group, a biphenyl group, a terphenyl group, or any combination thereof.
8. The organometallic compound of claim 1, wherein
a4 is not 0, and
an *-(L4)b4-(R4)c4 in a number of a4 satisfies Condition 3, Condition 4, Condition 5, or combination thereof:
Condition 3
R4 in a number of c4 is a substituted C6-C60 aryl group,
Condition 4
L4 is a C5-C30 carbocyclic group substituted with an R10a group,
Condition 5
L4 is a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group and R4 is not hydrogen.
9. The organometallic compound of claim 1, wherein
a51 and a52 are each independently 0, 1, or 2,
the sum of a51 and a52 is 1 or 2, and
a53 is 1 or 2.
10. The organometallic compound of claim 1, wherein,
in Formula 1,
a group represented by
Figure US20200115406A1-20200416-C01003
is a group represented by one of Formulae CY1(1) to CY1(8),
a group represented by
Figure US20200115406A1-20200416-C01004
is a group represented by one of Formulae CY2(1) to CY2(4),
a group represented by
Figure US20200115406A1-20200416-C01005
is a group represented by one of Formulae CY3(1) to CY3(24), and
a group represented by
Figure US20200115406A1-20200416-C01006
is a group represented by one of Formulae CY4(1) to CY4(74):
Figure US20200115406A1-20200416-C01007
Figure US20200115406A1-20200416-C01008
Figure US20200115406A1-20200416-C01009
Figure US20200115406A1-20200416-C01010
Figure US20200115406A1-20200416-C01011
Figure US20200115406A1-20200416-C01012
Figure US20200115406A1-20200416-C01013
Figure US20200115406A1-20200416-C01014
Figure US20200115406A1-20200416-C01015
Figure US20200115406A1-20200416-C01016
Figure US20200115406A1-20200416-C01017
Figure US20200115406A1-20200416-C01018
Figure US20200115406A1-20200416-C01019
Figure US20200115406A1-20200416-C01020
wherein, in Formulae CY1(1) to CY1(8), CY2(1) to CY2(4), CY3(1) to CY3(24), and CY4(1) to CY4(74),
X2 to X4, Y1, L1 to L4, b1 to b4, R1 to R4, and c1 to c4 are each independently the same as described in claim 1,
X31 is O, S, N(R31), C(R31)(R32), or Si(R31)(R32),
X41 is O, S, N(R41), C(R41)(R42), or Si(R41)(R42),
L1a and L1b are each independently the same as described in connection with L1 in claim 1,
R1a and R1b are each independently the same as described in connection with R1 in claim 1,
L3a and L3b are each independently the same as described in connection with L3 in claim 1,
R3a, R3b, R31, and R32 are each independently the same as described in connection with R3 in claim 1,
L4a to L4d are each independently the same as described in connection with L4 in claim 1,
R4a to R4d, R41, and R42 are each independently the same as described in connection with R4 in claim 1,
*-(L1)b1-(R1)c1, *-(L1a)b1-(R1a)c1, *-(L1b)b1-(R1a)c1, *-(L2)b2-(R2)c2, *-(L3)b3-(R3)c3, * (L3a)b3-(R3a)c3, *-(L3b)b3-(R3a)c3, *-(L4)b4-(R4)c4, *-(L4a)b4-(R4a)c4, *-(L4b)b4-(R4a)c4, *-(L4c)b4-(R4c)c4, and *-(L4d)b4-(R4d)c4 are not hydrogen, wherein * indicates a binding site to a neighboring atom,
in Formulae CY1(1) to CY1(8), *′ indicates a binding site to X1 in Formula 1,
in Formulae CY2(1) to CY2(4), CY3(1) to CY3(24), and CY4(1) to CY4(74), *′ indicates a binding site to M in Formula 1,
in Formulae CY1(1) to CY1(8), * indicates a binding site to Y3 in Formula 1,
in Formulae CY2(1) to CY2(4), * indicates a binding site to ring CY1 in Formula 1, and *″ indicates a binding site to ring CY3 in Formula 1,
in Formulae CY3(1) to CY3(24), *″ indicates a binding site to ring CY2 in Formula 1, and * indicates a binding site to T1 in Formula 1, and
in Formulae CY4(1) to CY4(74), * indicates a binding site to T1 in Formula 1.
11. The organometallic compound of claim 1, wherein,
in Formula 1,
a group represented by
Figure US20200115406A1-20200416-C01021
is a group represented by Formula CY4-1 or CY4-2:
Figure US20200115406A1-20200416-C01022
wherein, in Formulae CY4-1 and CY4-2,
X4, L4, b4, R4, and c4 are each independently the same as described in claim 1,
Z41 to Z44 are each independently the same as described in connection with R4 in claim 1,
′ indicates a binding site to M in Formula 1, and
indicates a binding site to T1 in Formula 1.
12. The organometallic compound of claim 10, wherein,
in Formula 1,
a group represented by
Figure US20200115406A1-20200416-C01023
is a group represented by Formula CY1 (1) or CY1 (6),
a group represented by
Figure US20200115406A1-20200416-C01024
is a group represented by Formula CY2(1),
a group represented by
Figure US20200115406A1-20200416-C01025
is a group represented by Formula CY3(3), and
a group represented by
Figure US20200115406A1-20200416-C01026
is a group represented by Formula CY4(3), CY4(4) or CY4(16).
13. The organometallic compound of claim 1, wherein
a group represented by
Figure US20200115406A1-20200416-C01027
in Formula 1 is a group represented by one of Formulae 51-1 to 51-32:
Figure US20200115406A1-20200416-C01028
Figure US20200115406A1-20200416-C01029
Figure US20200115406A1-20200416-C01030
Figure US20200115406A1-20200416-C01031
Figure US20200115406A1-20200416-C01032
wherein, in Formulae 51-1 to 51-32,
R51, R52, c52, A51, and A52 are each independently the same as described in claim 1,
R53 and c53 are each independently the same as described in connection with
R52 and c52 in claim 1,
c512 is an integer of 0 to 2,
c513 is an integer of 0 to 3, and
indicates a binding site to L51.
14. The organometallic compound of claim 1, wherein
the organometallic compound is represented by Formula 1-1 or 1-2:
Figure US20200115406A1-20200416-C01033
wherein, in Formulae 1-1 and 1-2
M, X1 to X4, Y1, Y3 to Y5, L4, L51, b4, b51, R51, R52, c51, c52, A51, A52, a51, a52 and a53 are each independently the same as described in claim 1,
Z11 to Z14 are each independently the same as described in connection with R in claim 1,
Z21 to Z23 are each independently the same as described in connection with R2 in claim 1,
Z31 to Z33 are each independently the same as described in connection with R3 in claim 1,
Z41 to Z44 are each independently the same as described in connection with R4 in claim 1,
two or more groups of Z11 to Z14 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of Z21 to Z23 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of Z31 to Z33 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group,
two or more groups of Z41 to Z44 are optionally linked to form a C5-C30 carbocyclic group that is unsubstituted or substituted with an R10a group or a C2-C30 heterocyclic group that is unsubstituted or substituted with an R10a group, and
R10a is the same as described in connection with R1.
15. The organometallic compound of claim 14, wherein
Z12, Z14, Z21 to Z23, Z31, Z33 and Z41 to Z44 are each independently hydrogen, deuterium, —CH3, or —CD3.
16. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and an organometallic compound of claim 1.
17. The organic light-emitting device of claim 16, wherein
the first electrode is an anode,
the second electrode is a cathode,
the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and
wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
18. The organic light-emitting device of claim 16, wherein
the emission layer comprises the organometallic compound.
19. The organic light-emitting device of claim 18,
wherein the emission layer further comprises a host, and an amount of the host is larger than an amount of the organometallic compound.
20. A diagnostic composition comprising an organometallic compound of claim 1.
US16/553,833 2018-08-31 2019-08-28 Organometallic compound, organic light-emitting device including the organometallic compound, and diagnostic composition including the organometallic compound Pending US20200115406A1 (en)

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